Methanol → Propanoic acid, 2-bromo-3-(phenylmethoxy)-, methyl ester

HRID 1943142Notes

Reaction equation

HRID 1943142 reaction equation
[Br:1][CH:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:19]O>>[Br:1][CH:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH3:19])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 109562653-(Benzyloxy)-2-bromopropanoic acid

Product 1

HCID 11011152Propanoic acid, 2-bromo-3-(phenylmethoxy)-, methyl esterYield 99%

Procedure

A solution of 2-bromo-3-[(phenylmethyl)oxy]propanoic acid (6 g, 23.2 mmol) in methanol (40 ml) at rt under argon was treated with thionyl chloride (1.7 ml, 23.2 mmol) and the reaction was then stirred at rt for 3 h and then evaporated to give product as a yellow oil (6.3 g, 99%).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-c81117c412504c65aeee6c5632869be6
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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