Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 415172

반응식

HRID 415172 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

생성물 1

HCID 256687Methyl 4-(bromomethyl)benzoate수율 98.8%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

Methyl 4-methylbenzoate 3 (2.9 g, 19.3 mmol) was dissolved in tetrachloromethane (CCl4, 20 mL) at room temperature. N-bromosuccinimide (NBS, 3.5 g, 19.0 mmol) and benzoyl peroxide (BPO, 0.26 g, 1.9 mmol) was added. The resulting mixture was stirred at reflux for 5 hr, then cooled to room temperature, washed with saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1) to get a white solid of methyl 4-(bromomethyl)benzoate (4.3 g, 97%), LC-MS (ESI) m/z 230 [M+1]+.

후처리

  1. temperatureat reflux for 5 hr
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried with anhydrous sodium sulfate and condensed under vacuum
  4. customThe residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1)

출처 및 근거

ORD 기록
ord-9a473a965e5e4d0b97aca180d7b8ba63
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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