Sodium Bromide → [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium bromide

HRID 616779Notes

Reaction equation

HRID 616779 reaction equation
[Cl-].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br-:28].[Na+]>O>[Br-:28].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 253881Sodium Bromide2×HCID 73680070[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

Product 1

HCID 73676660[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of 2.1 parts of [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride in 50 parts of water is added with stirring to 2 parts of sodium bromide. At the end of about 5 minutes an additional 4 parts of sodium bromide is added and the mixture is stirred until precipitation is complete. The precipitate is isolated by filtration, thus affording [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium bromide. This product melts at 205°-209° C. and is characterized by 60 MHz nuclear magnetic resonance peaks in CDCl3 (deuterated chloroform) at 107 cps (multiplet), 170 cps (multiplet), 228 cps (multiplet), 329 cps (doublet, J≃18 cps) in addition to the aromatic protons, and by microanalytic determination of bromide.

Workup

  1. additionis added

Sources & evidence

ORD record
ord-bfd6228b2d3d496abb450e397b73108b
Source dataset
uspto-grants-1978_02
Patent number
US04075407

Reaction notes

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