Water → 2-Bromo-5-fluoroanisole

HRID 2175841Notes

Reaction equation

HRID 2175841 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[C:10]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 70180432-Bromo-5-fluoroanisole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-fluorophenol (50 g, 0.26 mol) in 300 mL of DMF was added K2CO3 (72.8 g, 0.520 mol) at one portion and MeI (44.6 g, 0.310 mol) was added dropwise at 0° C. After the mixture was stirred at r.t. for 3 hours, the reaction was poured into 1 L of water and extracted with EtOAc (300 mL×3). The combined organic layers were washed with water, brine, dried and concentrated to afford 1-bromo-4-fluoro-2-methoxybenzene.

Workup

  1. additionwas added dropwise at 0° C
  2. extractionextracted with EtOAc (300 mL×3)
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-27a62537fe174c3ba9272f55b0b44c88
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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