Diazomethane → Methyl 4-(bromomethyl)benzoate

HRID 2260825Notes

Reaction equation

HRID 2260825 reaction equation
[N+](=[CH2:3])=[N-].[Br:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1>C(Cl)Cl>[Br:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:3])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diazomethane was added slowly to a suspension of 10 g of 4-(bromomethyl)-benzoic acid in 50 ml of methylene chloride until a persistent yellow coloring of the medium was obtained and excess diazomethane was destroyed by the addition of acetic acid. The mixture was evaporated to dryness and the residue was washed with water and dried under reduced pressure at ambient temperature to obtain 9.25 g of the desired product melting at 54° C.

Workup

  1. customwas obtained
  2. customexcess diazomethane was destroyed by the addition of acetic acid
  3. customThe mixture was evaporated to dryness
  4. washthe residue was washed with water
  5. customdried under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-745997d9208e44959b9078bf98dcd0c7
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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