Triphenylphosphine → HCID 86634292, compound

HRID 1672659Notes

Reaction equation

HRID 1672659 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][C:31]#[C:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[C:25]([CH:28]=1)[CH2:26][Br:27]>ClCCl>[Br-:27].[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][C:31]#[C:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:38]=2)=[C:25]([CH:28]=1)[CH2:26][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67351737HCID 67351737, compound

Product 1

HCID 86634292HCID 86634292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

63.7 mg (0.24 mmol) of triphenylphosphine are dissolved in 2 ml of dichloromethane, 94 mg (0.24 mmol) of 5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]benzyl bromide, dissolved in 2 ml of dichloromethane, are added dropwise, and the mixture is stirred at room temperature overnight. The solvent is distilled out in vacuo, and the crystalline residue is stirred with petroleum ether. The resulting colorless crystals are filtered off with suction and dried on a clay dish. 109 mg (0.17 mmol, 69% of theory) of the title compound are obtained.

Workup

  1. additionare added dropwise
  2. distillationThe solvent is distilled out in vacuo
  3. stirringthe crystalline residue is stirred with petroleum ether
  4. filtrationThe resulting colorless crystals are filtered off with suction
  5. customdried on a clay dish

Sources & evidence

ORD record
ord-4d4efd75f75245f1868663b65ce7b3d9
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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