Benzyl Bromide → HCID 58764188, compound

HRID 859656Notes

Reaction equation

HRID 859656 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 1 N 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 1 N 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-e3aa209d26d443bbb2026f03780eb6f5
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

Loading…