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

HRID 1015730Notes

Reaction equation

HRID 1015730 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl: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]([Cl:22])=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 537575064-Chloro-3-(methylsulfonyl)benzenemethanol

Product 1

HCID 668774604-(Bromomethyl)-1-chloro-2-(methylsulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

(Step 1) Triphenylphosphine (2.38 g) was suspended in acetonitrile (30 ml), bromine (0.47 ml) was added, and the mixture was stirred for 30 min. [4-Chloro-3-(methylsulfonyl)phenyl]methanol (2.0 g) was added to the reaction mixture, and the mixture was stirred at 85° C. for 8 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-chloro-2-(methylsulfonyl)benzene (1.23 g).

Workup

  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)

Sources & evidence

ORD record
ord-8e5d6d92eab44fbf8d4cf8d07cffc909
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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