Triphenylphosphine → 4-(Bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene

HRID 447834노트

반응식

HRID 447834 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][C:24]=1[S:31]([CH3:34])(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>C(#N)C>[Br:20][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([F:22])=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:25]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 668778384-Fluoro-3-(methylsulfonyl)benzenemethanol

생성물 1

HCID 668776264-(Bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

(Step 1) Triphenylphosphine (3.21 g) was suspended in acetonitrile (50 ml), bromine (0.64 ml) was added, and the mixture was stirred for 30 min. [4-Fluoro-3-(methylsulfonyl)phenyl]methanol (2.5 g) was added to the reaction mixture, and the mixture was stirred at 85° C. for 20 hr, treated with aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:1) to give 4-(bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene (1.64 g). 1H NMR (300 MHz, CDCl3) 8 ppm 3.24 (3H, s), 4.49 (2H, s), 7.19-7.31 (1H, m), 7.62-7.74 (1H, m), 7.99 (1H, dd, J=6.50, 2.35 Hz).

후처리

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:1)

출처 및 근거

ORD 기록
ord-9d8465140fa548818ea2faaeb4f0fb2d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481569B2

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