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

HRID 447834ノート

反応式

HRID 447834 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-9d8465140fa548818ea2faaeb4f0fb2d
出典データセット
uspto-grants-2013_07
特許番号
US08481569B2

反応ノート

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