Trifluoroacetic acid → 2,5-Diisopropyl-1-bromo-benzene

HRID 586678Notes

Reaction equation

HRID 586678 reaction equation
FC(F)(F)C(O)=O.C([C:11]1([Br:21])[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[CH:12]1N)(C)C.[CH2:22](ON=O)[CH2:23][CH:24](C)C.O[PH2]=O>CCO>[CH:23]([C:16]1[CH:15]=[CH:14][C:13]([CH:17]([CH3:18])[CH3:19])=[CH:12][C:11]=1[Br:21])([CH3:24])[CH3:22]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8053Isoamyl NitriteHCID 4124402Phosphinic AcidHCID 22335738HCID 22335738, compound

Product 1

HCID 119589802,5-Diisopropyl-1-bromo-benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trifluoroacetic acid (75 mL was added to a solution of Intermediate 34 in EtOH (100 mL) at 0° C. After stirring for 10 min, iso-amylnitrite (100 mL) was then added and the mixture was stirred for another 70 min. H3PO2 (70 mL) was added slowly and the mixture was warmed to ambient temperature over 5 hours. After dilution with ethyl acetate and sodium bicarbonate solution, the organic layer was separated, dried and concentrated to give the title compound in a crude form (17 g). Purification of the crude product by Kugelrohr distillation gave the title compound in pure form (13 g, 44% yield over 4 steps from 1,3-di-iso-propyl-benzene) as a colorless oil:

Workup

  1. stirringthe mixture was stirred for another 70 min
  2. customAfter dilution with ethyl acetate and sodium bicarbonate solution, the organic layer was separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55a2fa4ef75c41aa96be375c7753a323
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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