Triphenylphosphonium bromide → HCID 86756460, compound

HRID 636767Notes

Reaction equation

HRID 636767 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7].[BrH:14].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Br-:14].[OH:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:2][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 80811Triphenylphosphonium bromideHCID 12489759Methyl 4-hydroxy-3-(hydroxymethyl)benzoate

Product 1

HCID 86756460HCID 86756460, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound obtained in (b) (182 mg, 1 mmol) was mixed successfully with 2 ml of acetonitrile and triphenylphosphine hydrobromide (361 mg, 1.05 mmol). After heating at reflux for one hour fifteen minutes, the reaction medium was cooled and evaporated to dryness, ethyl ether was added, the mixture was filtered and the precipitate was washed with ethyl ether. After drying in an oven, 470 mg of a white solid were obtained, equivalent to a yield of 93%. Its properties were as follows:

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for one hour fifteen minutes
  3. temperaturethe reaction medium was cooled
  4. customevaporated to dryness, ethyl ether
  5. additionwas added
  6. filtrationthe mixture was filtered
  7. washthe precipitate was washed with ethyl ether
  8. customAfter drying in an oven

Sources & evidence

ORD record
ord-c5d50007f1fa492999a94627e25deebf
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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