4-Bromophenol → 4-(2,3-Difluorophenyl)phenol

HRID 1289375

반응식

HRID 1289375 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(COC)OC.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 78084-BromophenolHCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2734333(2,3-Difluorophenyl)boronic acid

생성물 1

HCID 189208344-(2,3-Difluorophenyl)phenol수율 75%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

실험 절차

First, 34.6 g of 4-bromphenol, 37.9 g of 2,3-difluorophenylboronic acid, 380 ml of dimethoxyethane, 380 ml of water, 97.8 g of cesium carbonate, and 7 g of tetrakis(triphenylphosphine)palladium were placed in a 1 L flask. The mixture was stirred under reflux for 20 hours. The reaction mixture was poured into water and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1) and recrvstallized from hexane to obtain 30.9 g of 2,3-difluoro-4'-hydroxybiphenyl (Y: 75%). The compound thus obtained had a purity of 99.8% by GC and an m.p. of 132° C. to 134.4° C.

후처리

  1. temperatureunder reflux for 20 hours
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-7a826045604c4a2db7210bd703efeeed
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750213

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