Methyl iodide → Methyl 4-bromo-2-methylbenzoate

HRID 63479Notes

Reaction equation

HRID 63479 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.IC.[C:14](=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 995704-Bromo-2-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 103.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mechanically stirred mixture of 4-bromo-2-methyl-benzoic acid (100 g, 465 mmol), iodomethane (95 g, 670 mmol) and sodium bicarbonate (112 g, 1340 mmol) in DMF (325 mL) was heated at 80° C. overnight. The reaction mixture was cooled to room temperature and partitioned between water (1500 mL) and 4:1 hexanes:ethyl acetate (1500 mL). The organic layer was washed with water and dried (Na2SO4). The solvent was removed under vacuum to give 110 g of 4-bromo-2-methyl-benzoic acid methyl ester as an oil, in 100% yield; 1H NMR (DMSO-d6) δ 2.51 (s, 3H), 3.84 (s, 3H), 7.40-7.78 (m, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water (1500 mL) and 4:1 hexanes
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2d4a6887c7764804b1de388e92a5ddfc
Source dataset
uspto-grants-2016_09
Patent number
US09447070B2

Reaction notes

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