Triphenylphosphonium bromide → HCID 86634290, compound

HRID 1672651Notes

Reaction equation

HRID 1672651 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[CH2:18]O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BrH:22].[C:23]1([P:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[Br-:22].[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[CH2:18][P+:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 80811Triphenylphosphonium bromideHCID 57864382HCID 57864382, compound

Product 1

HCID 86634290HCID 86634290, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.80 g (20 mmol) of [2-(4-tert-butylbenzyloxy)-5-fluorophenyl]methanol are dissolved in 70 ml of acetonitrile, 6.56 g (19.5 mmol) of triphenylphosphine hydrobromide are added, and the suspension is stirred under reflux for 24 h. The solvent is mostly distilled out in vacuo, and the crystals which have separated out are stirred with diethyl ether, filtered off with suction, washed with petroleum ether and dried on a clay dish. The resulting crude product is purified by preparative HPLC. 2.64 g (4.3 mmol, 21% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 24 h
  2. distillationThe solvent is mostly distilled out in vacuo
  3. customthe crystals which have separated out
  4. stirringare stirred with diethyl ether
  5. filtrationfiltered off with suction
  6. washwashed with petroleum ether
  7. customdried on a clay dish
  8. customThe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-400d89db7fb545c580b77d2fad5f8135
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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