Triphenylphosphine → HCID 86718423, compound

HRID 1025912Notes

Reaction equation

HRID 1025912 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8](O)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]C(Br)(Br)C(C(Br)(Br)Br)=O>C(Cl)Cl>[Br:33][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:13])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 13782678Hexabromopropan-2-oneHCID 64712604HCID 64712604, compound

Product 1

HCID 86718423HCID 86718423, compoundYield 164.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-chloro-2-fluorophenyl)butan-1-ol (CAS [1340262-68-1], 1.42 g, 7 mmol) in methylene chloride (35 mL) at RT was added triphenylphosphine (2.76 g, 10.5 mmol). After stirring for 15 min, 1,1,1,3,3,3-hexabromoacetone (1.86 g, 3.5 mmol) was added and stirred for 16 h. The reaction mixture was concentrated and the residue was purified by MPLC (100% hexanes) to yield 1.53 g of 1-(1-bromobutyl)-3-chloro-2-fluorobenzene as a colorless oil.

Workup

  1. stirringstirred for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by MPLC (100% hexanes)

Sources & evidence

ORD record
ord-1515ac90f57f46f8a47cb66631b231c1
Source dataset
uspto-grants-2014_05
Patent number
US08729110B1

Reaction notes

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