Water → HCID 58439109, compound

HRID 217441Notes

Reaction equation

HRID 217441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([CH3:12])[CH2:10]O)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)Cl>[Br:13][CH2:10][C@@H:9]([CH3:12])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 15786101HCID 15786101, compound

Product 1

HCID 58439109HCID 58439109, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-3-(4-chlorophenyl)-2-methylpropan-1-ol (300 mg) in DCM (20 mL) were added N-bromosuccinimide (347 mg) and triphenylphosphine (511 mg) under ice-cooling. The reaction liquid was stirred at room temperature for 2 hours, and then the reaction liquid was poured into water, followed by extraction with chloroform. The organic layer was washed with brine and dried over MgSO4, and then vehicle was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:EtOAc=100:0 to 90:10) to obtain 1-[(2S)-3-bromo-2-methylpropyl]-4-chlorobenzene (373 mg) as a colorless liquid.

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. customthe reaction liquid
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customvehicle was evaporated under reduced pressure

Sources & evidence

ORD record
ord-14fd502cd99d4d378c5f0efb46090aff
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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