Water → HCID 66674996, compound

HRID 422561Notes

Reaction equation

HRID 422561 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([SH:9])=[C:4]([F:10])[CH:3]=1.[H-].[Na+].I[CH3:14].O>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9][CH3:14])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 50997993HCID 50997993, compound

Product 1

HCID 66674996HCID 66674996, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromo-2-fluoro-5-methylbenzenethiol (2.28 g, 10.3 mmol) in 25 mL of DMF at RT was treated with NaH (0.284 g, 12.4 mmol). After 15 minutes the solution was cooled to 0° C. and iodomethane (0.772 mL, 12.4 mmol) was added. The reaction mixture was allowed to warm up to RT and stirred overnight. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (2.40 g, 99% yield) as an orange oil. The crude material was used in the next step without further purification.

Workup

  1. temperatureto warm up to RT
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06882ece26ce45cf97db04f4fd56706e
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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