Carbon tetrabromide → Methyl 4-(bromomethyl)benzoate

HRID 1084679Notes

Reaction equation

HRID 1084679 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[Br:14][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoateYield 142.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10 g of methyl 4-hydroxymethylbenzoate and 80 g of carbon tetrabromide in 300 ml of diethyl ether was added 63.2 g of triphenylphosphine. The reaction was warmed to room temperature overnight, filtered through Celite® and concentrated to 87.2 g of a yellow oil. Chromatography on silica gel (95:5, hexane:ethyl acetate) afforded 19.62 g of a white solid, m.p. 52° to 55° C.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated to 87.2 g of a yellow oil

Sources & evidence

ORD record
ord-75585dc5a73c4539a8f56146b874cb3b
Source dataset
uspto-grants-1991_04
Patent number
US05006524

Reaction notes

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