Bromine → HCID 21470010, compound

HRID 486284Notes

Reaction equation

HRID 486284 reaction equation
[Br:1]Br.[Cl-].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH2:13][P+:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[Br-:1].[Br:1][C:10]1[C:5]([OH:4])=[C:6]([CH2:13][P+:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 21470013HCID 21470013, compound

Product 1

HCID 21470010HCID 21470010, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the course of 1.5 hours, at 5°, 13 g of bromine are added dropwise to a solution of 35 g of [(2-hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride in 700 ml of methanol. The solution is concentrated in vacuo at 20° to 110 ml, 220 ml of ethyl acetate are added thereto in the course of 2 hours, the resulting yellow suspension is stirred for 2 hours at 0°, and the slightly yellow crystals are filtered off with suction and recrystallised from methanol. A mixture of colourless crystals (m.p.: 210°) which according to AgNO3 titre comprises 22.4 percent by weight [(3-bromo-2-hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride and 77.6 percent by weight [(3-bromo-2-hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium bromide is obtained; yield 76% of the theoretical yield.

Workup

  1. concentrationThe solution is concentrated in vacuo at 20° to 110 ml, 220 ml of ethyl acetate
  2. additionare added
  3. filtrationthe slightly yellow crystals are filtered off with suction
  4. customrecrystallised from methanol
  5. additionA mixture of colourless crystals (m.p.: 210°) which

Sources & evidence

ORD record
ord-7bde6aab27ce4c938890b3b645768882
Source dataset
uspto-grants-1994_03
Patent number
US05290939

Reaction notes

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