Bromine → Methyl 6-bromo-3-hydroxy-2-methylbenzoate

HRID 577547노트

반응식

HRID 577547 반응식
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:13]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Br:13][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:12])[C:2]([OH:1])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 12488879Methyl 3-hydroxy-2-methylbenzoate

생성물 1

HCID 77058981Methyl 6-bromo-3-hydroxy-2-methylbenzoate수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl 3-hydroxy-2-methylbenzoate (114a, 3.557 g, 21.40 mmol) in dichloromethane (100 mL) in a dry ice/acetonitrile bath (˜−45° C.) was added bromine (1.15 mL, 22.5 mmol) dropwise. The reaction was stirred at −45° C. for 2 hours before Na2S2O3 (sat. aq., 2 mL) was added. The reaction mixture was allowed to warm to room temperature. The reaction mixture was diluted with dichloromethane and washed with water. The dichloromethane layer was concentrated under vacuum, and the resulting crude product was purified by column chromatography (0-40% ethyl acetate/heptane) to give methyl 6-bromo-3-hydroxy-2-methylbenzoate (114b, 4.8 g, 92% yield) as a white solid.

후처리

  1. additionwas added
  2. washwashed with water
  3. concentrationThe dichloromethane layer was concentrated under vacuum
  4. customthe resulting crude product was purified by column chromatography (0-40% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-df2ba9b3fe8045e9b14c73f71d8c0c4d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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