Water → HCID 67461322, compound

HRID 554541Notes

Reaction equation

HRID 554541 reaction equation
C([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)C1C=CC=CC=1.O>ClCCl>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:10]2[S:11][C:12]([C:14]([F:15])([F:17])[F:16])=[CH:13][C:9]=2[OH:8])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 962WaterHCID 67459678HCID 67459678, compound

Product 1

HCID 67461322HCID 67461322, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-benzyloxy-2-(4-methoxybenzyl)-5-trifluoromethylthiophene (170.5 mg, 0.45 mmol) in dichloromethane (4.5 mL), a solution of boron tribromide-dimethylsulfide complex in dichloromethane (0.47 mL, 0.47 mmol) was added at −78° C. in a nitrogen stream. The reaction mixture was stirred at the same temperature for five minutes and then at 0° C. for 11 hours. To the reaction mixture, water was added and the resulting mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried (anhydrous sodium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (117.0 mg, 90%).

Workup

  1. waitat 0° C. for 11 hours
  2. extractionthe resulting mixture was extracted with methylene chloride
  3. washThe organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution and dried (anhydrous sodium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-8908ad9c6beb445a973bab3ac2293aff
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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