Triphenylphosphine → HCID 53991717, compound

HRID 1655765Notes

Reaction equation

HRID 1655765 reaction equation
[C:1]1([C@H:7]([CH:10]([CH3:12])[CH3:11])[CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C(Cl)Cl>[C:1]1([C@H:7]([CH:10]([CH3:12])[CH3:11])[CH2:8][Br:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11321150HCID 11321150, compound

Product 1

HCID 53991717HCID 53991717, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 49.3 g (0.3 mol) of (S)-(+) 2-phenyl-3-methylbutanol in 400 ml of absolute methylene chloride was treated with 80 g (0.3 mol) of triphenylphosphine. Thereafter, 53.4 g (0.3 mol) of N-bromosuccinimide were added portionwise while stirring vigorously. After 16 hours, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in hexane and purified by chromatography on silica gel, to obtain in this manner 34.9 g (51%) of (S)-(-)-2-phenyl-3-methylbromobutane as a volatile oil, [α]D20 =-19.6° (c=1%. chloroform).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in hexane
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-1567263d99424b41b4083b7cc5db097a
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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