Carbon tetrabromide → Methyl 3-(bromomethyl)benzoate

HRID 501815Notes

Reaction equation

HRID 501815 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C(Cl)Cl>[Br:33][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 155058Benzoic acid, 3-(hydroxymethyl)-, methyl ester

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.00 g of methyl 3-(hydroxymethyl)benzoate was dissolved in 80 mL of methylene chloride, to which 9.47 g of triphenylphosphine was added in small portions in an ice bath followed by addition of 12.00 g of carbon tetrabromide in small portions, and this solution was stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to yield 5.02 g of methyl 3-(bromomethyl)benzoate as colorless oil.

Workup

  1. additionwas added in small portions in an ice bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1]

Sources & evidence

ORD record
ord-bc01aedb6abe4ab7ab8d59fa0ae6f3df
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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