Triphenylphosphine → 1-Bromo-2(R)-isopropyl-3-(p-tert-butyl-phenyl)-propane

HRID 744775Notes

Reaction equation

HRID 744775 reaction equation
[CH:1]([C@@H:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1)[CH2:5]O)([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>ClCCl>[Br:37][CH2:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 228657362(R)-(p-tert-butyl-benzyl)-3-methyl-butanol

Product 1

HCID 228657311-Bromo-2(R)-isopropyl-3-(p-tert-butyl-phenyl)-propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.3 g of 2(R)-isopropyl-3-(p-tert-butyl-phenyl)-propanol in 50 ml of dichloromethane there are added, with stirring at 0° C., 3.15 g of triphenylphosphine and then, in portions, 2.14 g of N-bromosuccinimide. The reaction mixture is subsequently stirred for 16 hours at room temperature and is then concentrated by evaporation. The residue is purified by FC (100 g of silica gel, eluant; dichloromethane/hexane=1:1). The title compound is obtained: Rf (hexane)=0.49.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 16 hours at room temperature
  2. concentrationis then concentrated by evaporation
  3. customThe residue is purified by FC (100 g of silica gel, eluant; dichloromethane/hexane=1:1)

Sources & evidence

ORD record
ord-049a2783bba64cd0ad1523d6c982c218
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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