Phenol → 1-Bromo-2-fluoro-4-(1-phenoxyethyl)benzene

HRID 1501209

반응식

HRID 1501209 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[F:11].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:9])=[CH:4][C:3]=1[F:11]

참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 717565421-(4-Bromo-3-fluorophenyl)ethan-1-ol

생성물 1

HCID 1185627341-Bromo-2-fluoro-4-(1-phenoxyethyl)benzene수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 1-(4-bromo-3-fluorophenyl)ethanol (1 g, 4.58 mmol), phenol (474 mg, 4.58 mmol), and triphenyl phosphine (2.4 g, 6.88 mmol) was stirred in dry tetrahydrofuran (40 mL) under nitrogen atmosphere. After 1 h, the mixture was cooled to 0° C. Diisopropyl azodicarboxylate (2.3 g, 6.88 mmol) was added with drop-wise method and the reaction was stirred at room temperature for 18 hours. The solvent was evaporated and the residue was purified by column chromatography (silica gel, petroleum ether) to get 1-bromo-2-fluoro-4-(1-phenoxyethyl)benzene (900 mg, 89%).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (silica gel, petroleum ether)

출처 및 근거

ORD 기록
ord-c1269fa2f8c147b7a8ad9d876f1f5c61
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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