Methyl iodide → methyl 3-bromo-5-fluoro-2-methylbenzoate

HRID 1809468Notes

Reaction equation

HRID 1809468 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([OH:13])=[O:12].IC>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[C:9]([CH3:18])=[C:10]([CH:14]=[C:15]([F:17])[CH:16]=1)[C:11]([O:13][CH3:1])=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666439353-bromo-5-fluoro-2-methylbenzoic acid

Product 1

HCID 68633230methyl 3-bromo-5-fluoro-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (1.2 eq.) was added to a solution of (E3) in DMF (0.26 M) and the resulting suspension was stirred at RT for 30 min. Then, iodomethane (1.2 eq.) was added and the reaction mixture was stirred at RT overnight. The solution was diluted in EtOAc and the organic phase was washed with brine and dried (Na2SO4). Solvent was removed in vacuo giving a residue that was purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49) yielding (31% over 4 steps) the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 7.74 (1H, dd, J=8.4 and 2.8 Hz), 7.60 (1H, dd, J=7.3 and 2.5 Hz), 3.95 (3H, s), 2.59 (3H, s).

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed in vacuo
  5. customgiving a residue that
  6. customwas purified by flash chromatography column on silica (EtOAc/Petroleum ether 1:49)

Sources & evidence

ORD record
ord-df9a953acf33455baf3f7683c448a36a
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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