Boron tribromide → 4-Fluoro-3-(hydroxymethyl)phenol

HRID 1794054

반응식

HRID 1794054 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].FC1C=CC(OC)=CC=1C=O.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 5872472-Fluoro-5-hydroxybenzaldehydeHCID 27348722-Fluoro-5-methoxybenzaldehyde

생성물 1

HCID 691416144-Fluoro-3-(hydroxymethyl)phenol

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2-Fluoro-5-hydroxybenzyl alcohol was prepared according to the following procedure: 2-Fluoro-5-hydroxybenzaldehyde: to a stirred solution of 2-fluoro-5-methoxybenzaldehyde (18.3 g) in dichloromethane (200 mL) at 0° C. was added dropwise a solution of boron tribromide in dichloromethane (1M, 120 mL, 1 eq.). The mixture was stirred for 3 h then concentrated to a volume of ˜50 mL and partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was washed (water), dried (magnesium sulfate) and concentrated to give a red oil (22.7 g). The oil was purified by column chromatography (SiO2, DCM→DIPE) to give the product as a pink crystalline solid (9.9 g, 59% yield);

후처리

  1. concentrationthen concentrated to a volume of ˜50 mL
  2. custompartitioned between ethyl acetate (500 mL) and water (500 mL)
  3. washThe organic layer was washed (water)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dc884d24ad0149bc9a26ea2ecdad2a09
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022707B2

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