Water → HCID 86620290, compound

HRID 422553Notes

Reaction equation

HRID 422553 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[H-].[Na+].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[S:15].O>CN(C=O)C>[CH3:12][N:13]([CH3:17])[C:14](=[S:15])[O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 728574-Bromo-m-cresol

Product 1

HCID 86620290HCID 86620290, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromo-3-methylphenol (8.15 g, 43.6 mmol) in DMF (250 mL) at RT was treated with a suspension of NaH (1.25 g, 52.3 mmol) in 10 mL of DMF. After 15 minutes the solution was cooled to 0° C. and dimethylthiocarbamoyl chloride (8.08 g, 65.4 mmol) was added. The reaction mixture was warmed up to 80° C. and stirred for 45 minutes. After cooling to RT, the mixture was poured into water (1 L). The aqueous layer was extracted with EtOAc (3×200 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a yellow oil. The crude yellow oil material was purified by silica gel chromatography (5-50% EtOAc in hexanes) to afford 6.87 g of O-4-bromo-3-methylphenyl dimethylcarbamothioate as a clear, colorless oil. MS+=276.0 (M+H)

Workup

  1. temperatureThe reaction mixture was warmed up to 80° C.
  2. temperatureAfter cooling to RT
  3. extractionThe aqueous layer was extracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe crude yellow oil material was purified by silica gel chromatography (5-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6def8cbba9604b4f86f93462813e2d2d
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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