Diazomethane → Methyl 4-bromo-2-chloro-6-methylbenzoate

HRID 2427492Notes

Reaction equation

HRID 2427492 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:12])[CH:3]=1.[N+](=[CH2:15])=[N-]>C(OCC)(=O)C.C(OCC)C>[CH3:15][O:7][C:6](=[O:8])[C:5]1[C:9]([CH3:11])=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[Cl:12]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 566042464-Bromo-2-chloro-6-methylbenzoic acid

Product 1

HCID 45480505Methyl 4-bromo-2-chloro-6-methylbenzoateYield 113%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-chloro-6-methylbenzoic acid (1.10 g, 4.41 mmol) was dissolved in ethyl acetate (15 mL). A solution of diazomethane in diethyl ether was added until the yellow colour persisted. After fifteen minutes the reaction was quenched with acetic acid. After one hour, the mixture was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to provide the title compound as a yellow oil (1.31 g, 113%). 1H NMR CDCl3: 7.43 (s, 1H), 7.31 (s, 1H), 3.94 (s, 3H), 2.33 (s, 3H).

Workup

  1. customAfter fifteen minutes the reaction was quenched with acetic acid
  2. washthe mixture was washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed3020889ad43c7bf69b2e437b5e85d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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