Bromine → HCID 86682804, 화합물

HRID 1504328노트

반응식

HRID 1504328 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH2:13][OH:14].[Br:15]Br>S(=O)(=O)(O)O.O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:15][C:6]1[C:5]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:4][C:3]([CH2:13][OH:14])=[C:2]([Cl:1])[CH:7]=1

참가 물질

6

반응물 2

HCID 24408BromineHCID 717442072-Chloro-5-trifluoromethoxybenzyl alcohol

생성물 1

HCID 86682804HCID 86682804, 화합물수율 27.3%

시약·촉매·용매 3

HCID 178418844HCID 178418844, 화합물촉매HCID 962Water용매HCID 1118Sulfuric Acid용매

실험 절차

To a solution of (2-chloro-5-trifluoromethoxy-phenyl)-methanol (16.3 g, 71.94 mmol) in sulfuric acid (200 mL) and water (60 mL) was added bromine (12.65 g, 79.13 mmol), followed by silver sulfate (12.34 g, 39.57 mmol). The reaction mixture was stirred at RT for 1 h, poured onto ice, and then extracted with EtOAc (3×100 mL). The organic layers were combined, dried over Na2SO4 and concentrated to afford crude product, which was purified by flash chromatography (0-10% EtOAc in petroleum ether) to give the title intermediate (6.0 g, 27% yield). (m/z): [M−OH]+ calcd for C8H5BrClF3O2 286.91; 288.91. found 289.0.

후처리

  1. additionpoured onto ice
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto afford crude product, which
  6. customwas purified by flash chromatography (0-10% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-9c0f8639466e4538bba5d763f3fbf189
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212168B2

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