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

HRID 577547ノート

反応式

HRID 577547 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 77058981Methyl 6-bromo-3-hydroxy-2-methylbenzoate収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-df2ba9b3fe8045e9b14c73f71d8c0c4d
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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