Phosphine, triphenyl-, hydrobromide → HCID 66934025, compound

HRID 1019606Notes

Reaction equation

HRID 1019606 reaction equation
[Br-].[C:2]1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:31]([O:33][C:34]([N:36]1[CH2:42][CH2:41][C:40]2[C:43](Br)=[C:44]([C:46](=O)[C:47]([F:50])([F:49])[F:48])[S:45][C:39]=2[CH2:38][CH2:37]1)=[O:35])[CH3:32]>C1COCC1.CCOC(C)=O>[CH2:31]([O:33][C:34]([N:36]1[CH2:42][CH2:41][C:40]2[CH:43]=[C:44]([C:46]([C:47]([F:50])([F:49])[F:48])=[CH2:2])[S:45][C:39]=2[CH2:38][CH2:37]1)=[O:35])[CH3:32]

Participants

6

Reactant 3

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 67197583HCID 67197583, compound

Product 1

HCID 66934025HCID 66934025, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Triphenyl phosphonium bromide (393 mg, 1.1 mmol) was stirred in 7 mL THF. KHMDS (199 mg, 1.0 mmol) was added and the yellow solution was stirred for 30 minutes at room temperature. The product of step (a) (180 mg, 0.56 mmol) was dissolved in 7 mL THF and added to the above reaction. The solution was allowed to stir for 1 hour at room temperature, then diluted with EtOAc (25 mL) and washed with water (2×20 mL). The crude product was purified by silica gel chromatography (30% EtOAc in Hex) to give 100 mg of the sub-title compound.

Workup

  1. additionadded to the above reaction
  2. stirringto stir for 1 hour at room temperature
  3. washwashed with water (2×20 mL)
  4. customThe crude product was purified by silica gel chromatography (30% EtOAc in Hex)

Sources & evidence

ORD record
ord-2ba908d0c0ef4e80b604bdf248841611
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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