3-Acetylphenylboronic acid → (E)-3-(3'-acetyl-biphenyl-4-yl)-but-2-en-1-ol

HRID 984342Notes

Reaction equation

HRID 984342 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Br[C:14]1[CH:19]=[CH:18][C:17](/[C:20](/[CH3:24])=[CH:21]/[CH2:22][OH:23])=[CH:16][CH:15]=1>>[C:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17](/[C:20](/[CH3:24])=[CH:21]/[CH2:22][OH:23])=[CH:16][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27343103-Acetylphenylboronic acidHCID 69361278(E)-3-(4-bromophenyl)but-2-en-1-ol

Product 1

HCID 69799799(E)-3-(3'-acetyl-biphenyl-4-yl)-but-2-en-1-ol

Procedure

3-Acetylphenylboronic acid (7.10 g, 43.3 mmol) was coupled with (E)-3-(4-bromophenyl)-but-2-en-1-ol (5.76 g, 25.0 mmol) by a procedure analogous to that described in example 54 a to give (E)-3-(3′-acetyl-biphenyl-4-yl)-but-2-en-1-ol as an off-white solid; 5.33 g (79%). This solid was recrystallised from aqueous ethanol to give a first crop of very pure (E)-3-(3′-acetyl-biphenyl-4-yl)-but-2-en-1-ol as colourless platelets; 2.78 g (41%) and a second crop of (E)-3-(3′-acetyl-biphenyl-4-yl)-but-2-en-1-ol as an amorphous off-white solid; 2.53 g (37%).

Sources & evidence

ORD record
ord-8a2cc08a5414480eb748c8f254ba1fdb
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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