Bromine → Methyl 3-bromo-2-hydroxy-6-methylbenzoate

HRID 2177758Notes

Reaction equation

HRID 2177758 reaction equation
[Br:1]Br.[CH3:3][CH:4]1[CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:8](=[O:14])[CH:7]=[CH:6][CH2:5]1>C(O)(=O)C>[Br:1][C:7]1[C:8]([OH:14])=[C:9]([C:4]([CH3:3])=[CH:5][CH:6]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 15581456Methyl 6-methyl-2-oxocyclohex-3-ene-1-carboxylate

Product 1

HCID 66685369Methyl 3-bromo-2-hydroxy-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (16.8 ml) in acetic acid (150 ml) was added dropwise to a stirred and cooled solution of methyl 6-methyl-2-oxocyclohex-3-enecarboxylate (prepared according to Hauser et al, Synthesis 1980 814, 28.2 g) in acetic acid at 0° C. The resultant mixture was stirred and heated at reflux for 24 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with sodium bicarbonate (saturated aqueous solution) and brine, then dried (MgSO4 and activated charcoal) and filtered through Celite. The filtrate was evaporated to dryness to give methyl 3-bromo-2-hydroxy-6-methylbenzoate (30.8 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with sodium bicarbonate (saturated aqueous solution) and brine
  7. dry with materialdried (MgSO4 and activated charcoal)
  8. filtrationfiltered through Celite
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-36ea2ea8a7ff47baac90697627114255
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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