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Tributylphosphine → o-Methoxycarbonylbenzyltributylphosphonium bromide

HRID 972556
Notes
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Reaction equation

HRID 972556 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[Br:13]CC1C(C(OC)=O)=CC=CC=1.[CH2:25]([P:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28].[Br-].[Na+]>O.C(#N)C>[Br-:13].[CH3:12][O:11][C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][P+:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 118590Methyl 2-chloromethylbenzoateHCID 253881Sodium BromideHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 21388625o-Methoxycarbonylbenzyltributylphosphonium bromide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

To a suitable vessel containing about 16.2 g of an approximate 50:50 mixture of methyl α-chloro-o-toluate and methyl α-bromo-o-toluate is added 100 ml of acetonitrile and 17.2 g (0.085 mol) of tributylphosphine and held at reflux under nitrogen for about 45 minutes. The solvent is removed under vacuum and the residue is dissolved in 370 ml of water. The aqueous solution is extracted twice with ether and added to a solution of 102 g (1.0 mol) of sodium bromide in 150 ml of water. This mixture is extracted with three 150 ml portions of chloroform. The chloroform extracts are combined, dried over calcium sulfate and concentrated under vacuum to 36.3 g of colorless oil. Two triturations of this oil with ether provides a white solid which upon recrystallization from ethyl acetate-ether yields approximately 24.6 g of o-methoxycarbonylbenzyltributylphosphonium bromide having a melting point of 65°-66°.

Workup

  1. additionTo a suitable vessel containing
  2. temperatureat reflux under nitrogen for about 45 minutes
  3. customThe solvent is removed under vacuum
  4. dissolutionthe residue is dissolved in 370 ml of water
  5. extractionThe aqueous solution is extracted twice with ether
  6. extractionThis mixture is extracted with three 150 ml portions of chloroform
  7. dry with materialdried over calcium sulfate
  8. concentrationconcentrated under vacuum to 36.3 g of colorless oil
  9. customTwo triturations of this oil with ether provides a white solid which
  10. customupon recrystallization from ethyl acetate-ether

Sources & evidence

ORD record
ord-405fd26bf5b84149980f9811d3f73997
Source dataset
uspto-grants-1977_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04053501

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes