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

HRID 1438119Notes

Reaction equation

HRID 1438119 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 23A (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 23B 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-99825fd4d601453e9d363a946997b53e
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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