2,4-Bis(trifluoromethyl)bromobenzene → HCID 86600707, compound

HRID 1820735Notes

Reaction equation

HRID 1820735 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1Br.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CC([O-])(C)C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[C:2]([F:15])([F:14])[F:1])[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 1361642,4-Bis(trifluoromethyl)bromobenzeneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 86600707HCID 86600707, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5 mmol 2,4-bis(trifluoromethyl)bromobenzene, 6 mmol N-BOC-piperazine, 8 mmol NaOtBu, 0.5 mmol rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 1 mmol tris-(dibenzylideneacetone)dipalladium chloroform complex in 20 ml toluene was stirred at 80° C. for 3 hours. The mixture was then diluted with water, extracted with ethyl acetate, dried and purified by column chromatography (SiO2; cyclohexane/ethyl acetate 9:1) to yield the title compound as a yellowish oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. custompurified by column chromatography (SiO2; cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-4ced93b2cb874d82b0d4659a009e2b90
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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