Methyl iodide → (2-Chloro-6-fluoro-4-methoxyphenyl)methanol

HRID 1772875Notes

Reaction equation

HRID 1772875 reaction equation
CI.[Cl:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11].[C:14](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([O:13][CH3:14])[CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 222200093-Chloro-5-fluoro-4-(hydroxymethyl)phenol

Product 1

HCID 84771656(2-Chloro-6-fluoro-4-methoxyphenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.13 mL, 2.08 mmol) was added dropwise to a solution of 3-chloro-5-fluoro-4-(hydroxymethyl)phenol (334 mg, 1.89 mmol) and potassium carbonate (287 mg, 2.08 mmol) in DMF (5 mL) and the reaction mixture stirred for 4 h at rt. The reaction mixture was partitioned between DCM and H2O, the organic layer separated and the aqueous further extracted with DCM. The combined organic phases were concentrated in vacuo to yield the title compound as a yellow oil (360 mg, 1.89 mmol).

Workup

  1. customThe reaction mixture was partitioned between DCM and H2O
  2. customthe organic layer separated
  3. extractionthe aqueous further extracted with DCM
  4. concentrationThe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-bc9740bfbae847569450f1f5e71b7003
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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