Triphenylphosphine → [1-(Bromomethyl)cyclopropyl]methoxymethylbenzene

HRID 863296Notes

Reaction equation

HRID 863296 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:13]O)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C:10]1([CH2:13][Br:34])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 19697866[1-[(Benzyloxy)Methyl]cyclopropyl]Methanol

Product 1

HCID 19697561[1-(Bromomethyl)cyclopropyl]methoxymethylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

58.9 g of 1-benzyloxymethyl-1-(hydroxymethyl)cyclopropane and 88.5 g of triphenylphosphine are dissolved in 600 ml of methylene chloride, and 60 g of N-bromosuccinimide are added in portions at 0° C. The reaction mixture is stirred at room temperature for 16 h and concentrated and the residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent. This gives 68 g of the pure title compound: Rf (1:1 mixture from methylene chloride and hexane)=0.50.

Workup

  1. concentrationconcentrated
  2. customthe residue is purified by means of FC over 3 kg of silica gel with a 1:1 mixture of methylene chloride and hexane as the eluting agent

Sources & evidence

ORD record
ord-f7d58b8cd47e4473983a52245b1983ce
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…