Boron tribromide → 5-Amino-2-cyclopropylphenol

HRID 383385노트

반응식

HRID 383385 반응식
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

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 593949554-cyclopropyl-3-Methoxyaniline

생성물 1

HCID 552846985-Amino-2-cyclopropylphenol수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

A solution of BBr3 in dichloromethane (4.47 mL of 1M, 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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-db370360d31a4afb82e32c5ecc8fa1f8
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367660B2

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