Tributylphosphine → {4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-acetic Acid Methyl Ester

HRID 984941Notes

Reaction equation

HRID 984941 reaction equation
C(P(CCCC)CCCC)CCC.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)=[CH:34][CH2:35]O)=[CH:29][CH:28]=1>C1COCC1>[CH3:25][O:24][C:22](=[O:23])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:35][CH:34]=[C:33]([C:30]2[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][CH:31]=2)[C:37]2[CH:38]=[CH:39][C:40]([Br:43])=[CH:41][CH:42]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 222703043,3-Bis-(4-bromophenyl)prop-2-en-1-ol

Product 1

HCID 10164759{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-acetic Acid Methyl EsterYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (504 mg, 2.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (404 mg, 2.0 mmol), methyl 4-hydroxyphenylacetate (250 mg, 1.5 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (552 mg, 1.5 mmol) in dry THF (10 ml), the mixture stirred for 1 h, filtered and concentrated in vacuo. The crude product was then purified by column chromatography on silica (toluene eluent). The purified product was suspended in petroleum ether, filtered to give 480 mg (62%) of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was then purified by column chromatography on silica (toluene eluent)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b29ddc4592994e9692b51603f618b63c
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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