Methyl iodide → 3-bromo-2,6-dimethylbenzoic acid

HRID 354538Notes

Reaction equation

HRID 354538 reaction equation
[CH3:1]C1C=CC=C(C)C=1C(O)=O.BrBr.[Br:14][C:15]1[C:16]([CH3:25])=[C:17]([C:21]([CH3:24])=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19].CI>C(O)(=O)C>[Br:14][C:15]1[C:16]([CH3:25])=[C:17]([C:21]([CH3:24])=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19].[Br:14][C:15]1[C:16]([CH3:25])=[C:17]([C:21]([CH3:24])=[CH:22][CH:23]=1)[C:18]([O:20][CH3:1])=[O:19]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 124392,6-Dimethylbenzoic acidHCID 24408BromineHCID 81671423-bromo-2,6-dimethylbenzoic acid

Product 2

HCID 81671423-bromo-2,6-dimethylbenzoic acidHCID 13135243methyl 3-bromo-2,6-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Bromo-2,6-dimethylbenzoic acid was prepared from 2,6-dimethylbenzoic acid by treatment with bromine in acetic acid; see Org. Synth. Coll., Vol. 3, 138 (1944). 3-Bromo-2,6-dimethylbenzoic acid was esterified with methyl iodide as described in Tet. Letters, 689 (1973) to give methyl 3-bromo-2,6-dimethylbenzoate.

Sources & evidence

ORD record
ord-f2da8eec490d41fa982c806b41cc61d4
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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