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

HRID 984403Notes

Reaction equation

HRID 984403 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-c97852fed5574e44aacc82274aa31b92
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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