Phenacyl bromide → (R)-2-Bromo-1-phenylethanol

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

Reactant 2

HCID 6259Phenacyl bromide

HCID 107572-Chloroacetophenone

Product 1

HCID 52694(R)-2-Bromo-1-phenylethanolYield 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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04857468

Reaction notes

Loading…