Sodium Hydroxide → HCID 67459044, compound

HRID 554558Notes

Reaction equation

HRID 554558 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[C:23]([F:25])[F:24])=[CH:18][CH:17]=1)C1C=CC=CC=1.B(Br)(Br)Br.C(Cl)Cl.CSC.B(F)(F)F.C(Cl)Cl.CSC.[OH-].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:24][C:23]([F:25])=[CH:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67459862HCID 67459862, compoundHCID 86625726HCID 86625726, compoundHCID 86625727HCID 86625727, compound

Product 1

HCID 67459044HCID 67459044, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, a solution of 1-benzyloxy-2-[4-(2,2-Difluorovinyl)benzyl]benzene (984.5 mg, 2.93 mmol) in methylene chloride (12 mL) was cooled to −78° C., and a boron tribromide-dimethylsulfide methylene chloride solution (1.0 M, 7.32 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for two minutes and under cooling with ice for two hours, and furthermore the boron trifluoride-dimethylsulfide methylene chloride solution (4.39 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for 3.5 hours, then a sodium hydroxide aqueous solution and a saturated sodium hydrogencarbonate aqueous solution was added thereto and the mixture was extracted with methylene chloride, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:7)] to obtain the title compound (647.5 mg, 90%).

Workup

  1. temperatureunder cooling with ice for two hours
  2. stirringThe reaction mixture was stirred at the same temperature for 3.5 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:7)]

Sources & evidence

ORD record
ord-b3da69fe5ed74625bc39244190539e11
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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