Benzoyl Peroxide → Ethyl 2-(bromomethyl)-5-chlorobenzoate

HRID 1640006노트

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HRID 1640006 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCCl>[Br:14][CH2:13][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21269135Ethyl 5-chloro-2-methylbenzoate

생성물 1

HCID 13272463Ethyl 2-(bromomethyl)-5-chlorobenzoate수율 69.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
75 °C

실험 절차

A mixture of ethyl 5-chloro-2-methylbenzoate (3.20 g, 16.1 mmol), N-bromosuccinimide (3.15 g, 17.7 mmol) and benzoyl peroxide (0.39 g, 1.61 mmol) in 1,2-dichloroethane (90 mL) was heated to 75° C. in an oil bath for 4 h. After this time, the mixture was cooled to room temperature and the organic layer was washed with water (45 mL) and brine (45 mL). The organic layer was then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (silica, 1:20 ethyl acetate/hexanes) afforded ethyl 2-(bromomethyl)-5-chlorobenzoate (3.09 g, 68%) as a clear oil: 1H NMR (500 MHz, CDC13) 7.94 (d, J=2.5 Hz, 1H), 7.46 (dd, J=8.5, 2.5 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 4.91 (s, 2H), 4.42 (q, J=7.0 Hz, 2H), 1.43 (t, J=7.0 Hz, 3H); ESI MS m/z 279 [(M+2)+H]+.

후처리

  1. temperatureAfter this time, the mixture was cooled to room temperature
  2. washthe organic layer was washed with water (45 mL) and brine (45 mL)
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (silica, 1:20 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-df0590a0be1340c3a625f52c44e55cf8
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110681B2

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