Methyl iodide → 2-Bromo-5-fluorothioanisole

HRID 657507Notes

Reaction equation

HRID 657507 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[SH:9].[C:10](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9][CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 190668612-Bromo-5-fluorobenzenethiol

Product 1

HCID 117700132-Bromo-5-fluorothioanisoleYield 88.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

76.61 g of 2-bromo-5-fluorothiophenol were dissolved in 740 ml of DMF and 62.23 g of potassium carbonate were added. A solution of 26.07 ml of iodomethane in 130 ml of DMF was then added dropwise at a temperature between 3° C. and 11° C. The reaction mixture was stirred for 3 h at room temperature, then diluted with 3 l of water and extracted four times with 500 ml each of MTB. The combined extracts were dried over sodium sulfate and the solvent was removed in vacuo. 72.71 g of the title compound were obtained as a pale brown oil.

Workup

  1. extractionextracted four times with 500 ml each of MTB
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ef15752e2d1843e5ac3b7c5e1935dcac
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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