Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

HRID 225986

반응식

HRID 225986 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 2

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

생성물 1

HCID 2734813Methyl 2-(bromomethyl)benzoate수율 95,246.602%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a mixture of methyl 2-methylbenzoate (5.0 g, 0.033 mmol) and N-bromosuccinimide (5.9 g, 0.033 mmol) in CCl4 (50 mL) was added benzoyl peroxide (0.04 g, 0.00016 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature, filtered through Celite, and concentrated to afford methyl 2-(bromomethyl)benzoate (7.2 g, ca. 94% mass recovery), which was contaminated with ca. 14% unreacted starting material and was used without purification.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationfiltered through Celite
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cf3f803730124b61b67889dd940bee60
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557135B2

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