Ammonium Chloride → HCID 67462534, compound

HRID 554557Notes

Reaction equation

HRID 554557 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[F:27][C:28]([F:38])=[CH:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.[Cl-].[NH4+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:34]([C:33]1[CH:32]=[CH:31][C:30]([CH:29]=[C:28]([F:27])[F:38])=[CH:37][CH:36]=1)[OH:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 86093485HCID 86093485, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 67462534HCID 67462534, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, a solution of 2-benzyloxybromobenzene (1.63 g, 6.18 mmol) in THF (4 mL) was cooled to −78° C., and an n-butyllithium hexane solution (2.44 M, 2.66 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for 25 minutes, and then a solution of 4-(2,2-difluorovinyl)benzaldehyde previously prepared in THF (1 mL) was added dropwise thereto. The reaction mixture was stirred at the same temperature for 1.25 hours, and then a saturated ammonium chloride aqueous solution and water was added thereto. The resulting mixture was extracted with ether and the organic layer was washed with a saturated ammonium 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 (1:5)] to obtain the title compound (1.17 g, 81%).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at the same temperature for 1.25 hours
  3. extractionThe resulting mixture was extracted with ether
  4. washthe organic layer was washed with a saturated ammonium 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 (1:5)]

Sources & evidence

ORD record
ord-d75b49b80aea4bbf8d9837d0dbd22366
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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