Bromine → HCID 21470010, compound

HRID 1938811Notes

Reaction equation

HRID 1938811 reaction equation
[Br:1]Br.[Br-:3].[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:3][C:10]1[C:5]([OH:4])=[C:6]([CH2:13][P+:14]([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)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 11576578Phosphonium, [(2-hydroxy-5-methoxyphenyl)methyl]triphenyl-, bromide

Product 1

HCID 21470010HCID 21470010, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the course of 1.5 hours, at 5°, 16 g of bromine are added dropwise to a solution of 50 g of [(2-hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium bromide in 11 of methanol. The solution is then concentrated in vacuo at 20° to 130 ml, 250 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. [(3-Bromo-2-hydroxy-5-methoxy-phenyl)-methyl]-triphenyl-phosphonium bromide is thus obtained in the form of colourless crystals [m.p.: 259°; IR (KBr): 2875, 1585, 1565, 1415, 1325, 1200, 1165, 1150 cm-1 ; 1H-NMR (360 MHz), DMSO-d6); 3.43 (s, 3H, OCH3), 5.03 (d, 2H, CH2P+), 6.42 (dd, 1H), 7.08 (dd, 1H, 7.61 to 7.80 (m, 12H), 7.92 (m, 3H), 9.00 (br, s, 1H, OH) ppm]; yield 76% of the theoretical yield

Workup

  1. concentrationThe solution is then concentrated in vacuo at 20° to 130 ml, 250 ml of ethyl acetate
  2. additionare added
  3. filtrationthe slightly yellow crystals are filtered off with suction
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-d9e7249b3255435fbdec7ed5b41646ff
Source dataset
uspto-grants-1997_12
Patent number
US05693807

Reaction notes

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