Benzyl Bromide → HCID 58764188, compound

HRID 2387045Notes

Reaction equation

HRID 2387045 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]([F:26])([F:25])[F:24])[C:17]=1[OH:27]>CN(C=O)C>[CH2:7]([O:27][C:17]1[C:18]([CH2:22][C:23]([F:24])([F:25])[F:26])=[CH:19][CH:20]=[CH:21][C:16]=1[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58764013HCID 58764013, compound

Product 1

HCID 58764188HCID 58764188, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (953 mg, 6.89 mmol) followed by benzyl bromide (0.8 mL, 6.89 mmol) were added to a solution of 2-methyl-6-(2,2,2-trifluoro-ethyl)-phenol (1.78 g, 6.89 mmol) in DMF (20 mL). The mixture was stirred at room temperature for 15 hours and then partitioned between H2O and EtOAc. The organic layer was washed with 1N HCl, brine, dried over Na2SO4 and concentrated to a brown oil. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the product as a clear oil (2.1 g). LCMS: APCI−VE=279

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-822b6c6ad17549fabd461dfd43d6f060
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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