Triphenylphosphine → 2-Butylhexylbromide

HRID 1748944Notes

Reaction equation

HRID 1748944 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:22]([CH:26]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:27]O)[CH2:23][CH2:24][CH3:25]>ClCCl>[CH2:22]([CH:26]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:27][Br:1])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 760052-Butylhexanol

Product 1

HCID 157526152-Butylhexylbromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (61.4 g, 384 mmol) was added into a solution of triphenylphosphine (100.7 g, 384 mmol) and 450 mL dichloromethane at room temperature under argon protection. Then 2-butylhexanol (60.8 g, 384 mmol) was added dropwise via additional funnel over 50 minutes, the reaction solution was kept to stir at room temperature overnight. Dichloromethane was evaporated, and the concentrate filtered with pentane wash. The filtrate was concentrated via rotary evaporation and the resulting crude yellow oil was purified via vacuum distillation. The title compound was collected as colorless oil (70.8 g, 83.3%). 1H NMR (CDCl3): δ 0.89-0.92 (6H, m), 1.21-1.45 (12H, m), 1.54-1.67 (1H, m), 3.45 (2H, d).

Workup

  1. customDichloromethane was evaporated
  2. filtrationthe concentrate filtered with pentane
  3. washwash
  4. concentrationThe filtrate was concentrated via rotary evaporation
  5. distillationthe resulting crude yellow oil was purified via vacuum distillation
  6. customThe title compound was collected as colorless oil (70.8 g, 83.3%)

Sources & evidence

ORD record
ord-5d8e40602d354cfca96066dfef8d497e
Source dataset
uspto-grants-2015_10
Patent number
US09153785B2

Reaction notes

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