Boron tribromide → 5-Amino-2-cyclopropylphenol

HRID 471955ノート

反応式

HRID 471955 の反応式
B(Br)(Br)Br.[CH:5]1([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[O:15]C)[CH2:7][CH2:6]1>ClCCl>[NH2:12][C:11]1[CH:13]=[CH:14][C:8]([CH:5]2[CH2:7][CH2:6]2)=[C:9]([OH:15])[CH:10]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 593949554-cyclopropyl-3-Methoxyaniline

生成物 1

HCID 552846985-Amino-2-cyclopropylphenol収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of BBr3 in dichloromethane (4.47 mL of 1 M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN 0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+.

後処理

  1. washThe reaction mixture was washed with aqueous NaHCO3, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by HPLC (10-99% CH3CN 0.05% TFA)

出典と根拠

ORDレコード
ord-6f6f9cd66a164c26bc5edcbbc8c04c4b
出典データセット
uspto-grants-2014_01
特許番号
US08633189B2

反応ノート

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