Ammonium Chloride → HCID 12010832, compound

HRID 1282473Notes

Reaction equation

HRID 1282473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:9](Br)[CH3:10])=[CH:4][CH:3]=1.C([Li])CCC.Cl[P:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:9]([P:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 66180ChlorodiphenylphosphineHCID 18424482HCID 18424482, compoundHCID 178418339Butyllithium

Product 1

HCID 12010832HCID 12010832, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

Into a reactor were introduced 0.907 g (2.93 mmol) of the 1,1-bis(4-fluorophenyl)-2-bromopropene and 20 mL of THF under a nitrogen atmosphere. The contents were cooled to −65° C., and 2.0 mL (2.9 mmol; 1.5 M hexane solution) of butyllithium was gradually added dropwise thereto. The resultant mixture was stirred for 40 minutes. Thereafter, a mixture of 0.58 mL (3.2 mmol) of chlorodiphenylphosphine and 5 mL of THF was added thereto, and the resultant mixture was stirred at that temperature for 2 hours and then heated to room temperature. Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from methanol to obtain 0.687 g (57%) of the target compound as white crystals.

Workup

  1. additionwas added
  2. temperatureheated to room temperature
  3. extractionwas then extracted with ethyl acetate
  4. washThe resultant organic layer was washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed under reduced pressure
  7. customThe concentrate was recrystallized from methanol

Sources & evidence

ORD record
ord-ef7e213598f845a1998865dc8210351c
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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