Methyl 4-methylbenzoate → Methyl 4-(bromomethyl)benzoate

HRID 1579701Notes

Reaction equation

HRID 1579701 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[Br:12]Br>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7455Methyl 4-methylbenzoateHCID 24408Bromine2×

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

574 g. of this ester were dissolved in 1200 ml. of carbontetrachloride and, while boiling and exposing to a U.V. lamp, treated dropwise with a solution of 109 ml. of bromine in 400 ml. of carbontetrachloride. After all of the bromine had been dropped in, the mixture was heated for a further hour, concentrated in vacuo and the residue crystallized from low boiling petroleum ether, yielding as colorless fine crystals, 4-(bromo-methyl)benzoic acid methyl ester, which melted at 52°. For the reaction of this ester with 1-methyl-1,2-dicarbobenzoxy-hydrazine, the following procedure was followed:

Workup

  1. additionlamp, treated dropwise with a solution of 109 ml
  2. temperaturewas heated for a further hour
  3. concentrationconcentrated in vacuo
  4. customthe residue crystallized

Sources & evidence

ORD record
ord-971d4bded4a0460b959cecfaa21b4b00
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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