Diisobutylaluminum hydride → (E)-3-(3',5'-dibromo-biphenyl-4-yl)-but-2-en-1-ol

HRID 1268342Notes

Reaction equation

HRID 1268342 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[CH:22][C:21](/[C:24](/[CH3:31])=[CH:25]/[C:26](OCC)=[O:27])=[CH:20][CH:19]=2)[CH:14]=[C:15]([Br:17])[CH:16]=1>>[Br:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:19]=[CH:20][C:21](/[C:24](/[CH3:31])=[CH:25]/[CH2:26][OH:27])=[CH:22][CH:23]=2)[CH:14]=[C:15]([Br:17])[CH:16]=1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22557684(E)-ethyl 3-(3',5'-dibromo-biphenyl-4-yl)-but-2-enoate

Product 1

HCID 69800831(E)-3-(3',5'-dibromo-biphenyl-4-yl)-but-2-en-1-ol

Procedure

The colourless gum (E)-3-(3′,5′-dibromo-biphenyl-4-yl)-but-2-en-1-ol was prepared by DIBAL-H reduction of (E)-ethyl 3-(3′,5′-dibromo-biphenyl-4-yl)-but-2-enoate as described for example 52b, with the purification of the product being carried out by preparative HPLC.

Workup

  1. customas described for example 52b, with the purification of the product

Sources & evidence

ORD record
ord-60c23cb0f29f426db77f5286ca6c3195
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

Loading…