Triphenylphosphine dibromide → 4-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl bromide

HRID 1007492Notes

Reaction equation

HRID 1007492 reaction equation
[CH:1]1([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:21]([CH2:22]O)=[CH:20][C:19]=4[C:30]([F:33])([F:32])[F:31])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:34]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[CH:1]1([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:21]([CH2:22][Br:34])=[CH:20][C:19]=4[C:30]([F:33])([F:32])[F:31])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromide2×HCID 590609614-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl alcohol

Product 1

HCID 226698794-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation is carried out in analogy to the procedure of Example VII from 2.0 g (4.18 mmol) of benzyl alcohol derivative from Example XXI and 2.82 g (6.69 mmol) of dibromotriphenylphosphorane in 40 ml of acetonitrile. After stirring for 3 hours at room temperature, 0.3 equivalent of dibromotriphenylphosphorane is again added. The mixture is additionally stirred for 5 hours at 70° C. and afterwards overnight at room temperature. The purification of the product is carried out on silica gel using toluene as eluent.

Workup

  1. customPreparation
  2. stirringThe mixture is additionally stirred for 5 hours at 70° C. and afterwards overnight at room temperature
  3. customThe purification of the product

Sources & evidence

ORD record
ord-cb7d2592398a405e958dd933132cd94a
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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