Triphenylphosphonium bromide → HCID 86756462, compound

HRID 636770Notes

Reaction equation

HRID 636770 reaction equation
[BrH:1].[C:2]1([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[CH2:32]O)[C:25]([O:27][CH3:28])=[O:26]>C(#N)C>[Br-:1].[OH:21][C:22]1[CH:23]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[CH:29]=[CH:30][C:31]=1[CH2:32][P+:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 80811Triphenylphosphonium bromideHCID 13013948Methyl 3-hydroxy-4-(hydroxymethyl)benzoate

Product 1

HCID 86756462HCID 86756462, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of triphenylphosphine hydrobromide (11.9 g, 34.7 mmol) and methyl 3-hydroxy-4-hydroxymethylbenzoate (6 g, 35 mmol) in acetonitrile (65 ml, was heated at reflux for 1.5 h. The solvent was removed on a rotary evaporator under vacuum and the resulting solid was diluted in ethyl ether (30 ml). The product was isolated by filtration. Its properties were as follows:

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. customThe solvent was removed on a rotary evaporator under vacuum
  4. additionthe resulting solid was diluted in ethyl ether (30 ml)
  5. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-50b91c65c8a8408fa3561519832a293f
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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