Methyl iodide → 4-Bromo-1-fluoro-2-methoxybenzene

HRID 1515503Notes

Reaction equation

HRID 1515503 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([O:8][CH3:10])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-

Product 1

HCID 136049094-Bromo-1-fluoro-2-methoxybenzeneYield 77.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 7A (3.3 g, 17.3 mmol) and K2CO3 (4.78 g, 34.6 mmol) in DMF (20 mL) was added methyl iodide (1.46 mL, 23.4 mmol) at rt. The mixture was heated at 40° C. for 2.0 h. After cooling to rt, it was diluted with diethyl ether, washed with water and brine, dried over MgSO4. The crude residue was purified by flash column chromatography (EtOAc:hexanes=1:6) to give 2.74 g (77%) of 7B as a viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.89 (s, 3H), 6.95-7.00 (m, 3H).

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe crude residue was purified by flash column chromatography (EtOAc:hexanes=1:6)

Sources & evidence

ORD record
ord-cb0dcd1e9b304b808e8620d61363b1b5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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