Methanol → Methyl 4-(bromomethyl)benzoate

HRID 979634Notes

Reaction equation

HRID 979634 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](Cl)=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:19][OH:20]>C(Cl)Cl>[CH3:19][O:20][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 50682894-Bromomethyl-benzoyl chloride

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 19.5 grams of alpha-bromo-p-toluoyl chloride in 100 ml of methylene chloride is added to a solution of 15.7 ml of triethylamine in 100 ml of methanol. The reaction mixture is stirred overnight at room temperature and then concentrated. The residue is dissolved in ether, washed with water and the ether evaporated to give the intermediate p-methoxycarbonylbenzyl bromide.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in ether
  3. washwashed with water
  4. customthe ether evaporated

Sources & evidence

ORD record
ord-31d77d212f434f98bcc00f0d70982635
Source dataset
uspto-grants-1987_05
Patent number
US04668727

Reaction notes

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