Carbon tetrabromide → HCID 12606990, compound

HRID 341756Notes

Reaction equation

HRID 341756 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][CH2:10][CH2:11]O)[CH:6]=[CH:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>N1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:35][CH2:11][CH2:10][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 156361032-[[3-(Trifluoromethyl)phenyl]amino]ethanol

Product 1

HCID 12606990HCID 12606990, compoundYield 258.8%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-trifluoromethylphenyl)ethanolamine (4.17 g) and triphenyl phosphine (5.50 g) were dissolved in dry pyridine (35 ml) and stirred at 0° C. To this solution was added, portionwise, carbon tetrabromide (7.08 g). Stirring was continued for 1 hour and the reaction mixture was left to stand at room temperature overnight. A little more triphenyl phosphine (0.20 g) was added, and when virtually all starting alcohol had been consumed the pyridine was removed under reduced pressure to leave a brown residue (14.10 g). This was chromatographed on silica gel, eluting with ethyl acetate/hexane (1:9) as eluant to give the title compound as a light brown oil, yield 3.35 g.

Workup

  1. additionTo this solution was added
  2. stirringStirring
  3. waitthe reaction mixture was left
  4. waitto stand at room temperature overnight
  5. customwhen virtually all starting alcohol had been consumed the pyridine
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-c2962ddc9659493684557a5774eb4c15
Source dataset
uspto-grants-1999_01
Patent number
US05856273

Reaction notes

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