p-Toluenesulfonic acid → HCID 86632014, compound

HRID 419697Notes

Reaction equation

HRID 419697 reaction equation
[N-]=[N+]=[N-].[Na+].Br[CH:6]([CH3:20])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=1)=[O:8].[N-:21]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>O1CCCC1>[C:43]1([CH3:53])[CH:44]=[CH:45][C:46]([S:49]([OH:52])(=[O:50])=[O:51])=[CH:47][CH:48]=1.[NH2:21][CH:6]([CH3:20])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=1)=[O:8]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 33558AzideHCID 86632015HCID 86632015, compound

Product 1

HCID 86632014HCID 86632014, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add sodium azide (640.94 mg; 1.05 equiv; 9.76 mmoles) in one portion to a solution of 2-Bromo-1-(4-fluoro-3-trifluoromethyl-phenyl)-propan-1-one (2.78 g; 1.00 equiv; 9.30 mmoles) in tetrahydrofuran (15 mL). Stir the mixture at room temperature overnight. Filter the solids and wash with THF. Add the crude azide (1.00 equiv; 9.30 mmoles; 2.43 g) to a solution of triphenylphosphine (1.06 equiv; 9.86 mmoles; 2.61 g) and p-Toluenesulfonic Acid (2.2 equiv; 20.47 mmoles; 3.56 g) in tetrahydrofuran (15 mL) under 20° C. Stir the mixture overnight. Filter the solid, then wash with THF to obtain 920 mg (24%) of the title compound.

Workup

  1. filtrationFilter the solids
  2. washwash with THF
  3. stirringStir the mixture overnight
  4. filtrationFilter the solid
  5. washwash with THF

Sources & evidence

ORD record
ord-030acf9c5cde408ab6a0d5232ec21d67
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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