Methane → ({3-Bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide

HRID 2061564Notes

Reaction equation

HRID 2061564 reaction equation
[Br-:1].[C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:30][C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[C:8]([CH2:10][P+:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1)#[N:3].C>CN(C=O)C>[Br-:1].[Br:1][C:6]1[C:7]([NH:30][C:31](=[O:36])[C:32]([F:34])([F:33])[F:35])=[C:8]([CH2:10][P+:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=[C:4]([C:2]#[N:3])[CH:5]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 86650873HCID 86650873, compound2×

Product 1

HCID 86650874({3-Bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

({5-Cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide (Intermediate 7, 32 g) was dissolved in DMF (150 mL) and decolorising charcoal (32 g) was added. The reaction mixture was stirred at room temperature for 2 hrs. The reaction mixture was then filtered washing with DMF (100 mL). N-Bromosuccinimide (34.9 g) was then added to the filtrate and the reaction mixture was then stirred at room temperature overnight. The reaction mixture was quenched with a saturated solution of sodium metabisulfite (500 mL) and stirred at room temperature for 30 min. The reaction mixture was then extracted with ethyl acetate (2×400 mL) and the organic extracts where combined, dried (MgSO4), filtered and the solvent was removed to give ({3-bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide as a crude product which was then used in the next reaction without further purification (37.2 g);

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered
  3. washwashing with DMF (100 mL)
  4. additionN-Bromosuccinimide (34.9 g) was then added to the filtrate
  5. stirringthe reaction mixture was then stirred at room temperature overnight
  6. customThe reaction mixture was quenched with a saturated solution of sodium metabisulfite (500 mL)
  7. stirringstirred at room temperature for 30 min
  8. extractionThe reaction mixture was then extracted with ethyl acetate (2×400 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-5062c0579f6d4e1c9de9fefc2e2bc4a2
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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