A kind of method for preparing benzoyl formate derivative
A technology of benzoyl formate and derivatives, which is applied in the field of preparation of benzoyl formate derivatives, can solve problems such as improper operation, low product yield, complicated operation, etc., and achieve mild conditions and good yield , the effect of simple operation
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Embodiment 1
[0032] The preparation method of embodiment 1 methyl benzoylformate
[0033] 54 mg (0.3 mmol) of alpha-methoxymethyl phenylacetate, 64 mg (0.36 mmol) of N-bromosuccinimide (NBS), were dissolved in 1 mL of ethyl acetate, and reacted for 1 hour under light conditions. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 42 mg of a colorless liquid with a yield of 86%.
[0034] Under the same conditions, using alpha-hydroxyphenylacetic acid methyl ester as a raw material, the reaction yield of methyl benzoylformate was 80%.
[0035] Methyl benzoylformate:
[0036] 1 H NMR (400MHz, CDCl 3 )δ: 8.01 (dd, J=8.3, 1.1 Hz, 2H), 7.69–7.62 (m, 1H), 7.50 (t, J=7.8Hz, 2H), 3.97 (s, 3H).
[0037] 13 C NMR (100MHz, CDCl 3 )δ: 186.02, 164.02, 134.94, 132.42...
Embodiment 2
[0038] The preparation method of embodiment 2 m-chlorobenzoylformic acid methyl esters
[0039] 59.6 mg (0.3 mmol) of methyl 2-(3-chlorophenyl)-2-methoxyacetate, N-bromosuccinimide (NBS) (0.36 mmol), dissolved in 1 mL of ethyl acetate, in Under light conditions, react for 3 hours. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 48 mg of white solid with a yield of 81%. Methyl m-chlorobenzoylformate:
[0040] 1 H NMR (400MHz, CDCl 3 )δ: 4.00(s, 3H), 7.47(t, J=7.9Hz, 1H), 7.64(dd, J=2.27, 7.9Hz, 1H), 7.93(d, J=8.1Hz, 1H), 8.03( s, 1H).
[0041] 13 C NMR (100MHz, CDCl 3 )δ: 53.0, 128.2, 129.8, 130.2, 133.9, 134.8, 135.2, 163.1, 184.4.
Embodiment 3
[0042] The preparation method of embodiment 3 p-chlorobenzoylformic acid methyl esters
[0043] 59.6 mg (0.3 mmol) of 2-(4-chlorophenyl)-2-methoxyacetic acid methyl ester, N-bromosuccinimide (NBS) (0.36 mmol), dissolved in 1 mL of ethyl acetate, in Under light conditions, react for 2 hours. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 52 mg of a white solid with a yield of 87%.
[0044] Under the same conditions, using methyl 2-(4-chlorophenyl)-2-hydroxyacetate as a raw material, the yield of methyl benzoylformate was 90%.
[0045] Methyl p-chlorobenzoylformate:
[0046] 1 H NMR (400MHz, CDCl 3 )δ: 3.99 (s, 3H), 7.50 (d, J=8.5Hz, 2H), 8.00 (d, J=8.5Hz, 2H).
[0047] 13 C NMR (100MHz, CDCl 3 )δ: 52.9, 129.4, 130.8, 131.4, 141.7, 163...
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Description
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Application Information
- IPC
- C07C69/738; C07C67/313
- CPC
- C07C67/313; C07C69/738
- Inventors
- 丸岡啓二; 徐伟平