Phenacyl bromide → (1S)-2-bromo-1-phenyl-ethanol

HRID 1722622Notes

Reaction equation

HRID 1722622 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].ClCC(C1C=CC=CC=1)=O>>[Br:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 107572-Chloroacetophenone

Product 1

HCID 52694(1S)-2-bromo-1-phenyl-ethanolYield 55.4%

Procedure

The procedure as in Example 3 was repeated except that 7.5 g of 2-bromo-acetophenone was employed as a substrate in place of 7.5 g of 2-chloro-acetophenone to give 4.2 g of (S)-2-bromo-1-phenyl ethanol (b.p. 85° C./0.5 mmHg). The product had a specific rotatory power [α]D25 +48.7° (C=1, chloroform) and an optical purity of 97% enantiomer excess by an HPLC analysis.

Sources & evidence

ORD record
ord-9fc6f468f052462385aae0e994d36900
Source dataset
uspto-grants-1989_08
Patent number
US04857468

Reaction notes

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