N-bromobutanimide → Ethyl 3-cyclopropyl-2-oxopropanoate

HRID 2190954Notes

Reaction equation

HRID 2190954 reaction equation
[CH:1]1([CH2:4][C:5]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])SCCCS2)[CH2:3][CH2:2]1.BrN1C(=[O:22])CCC1=O>>[CH:1]1([CH2:4][C:5](=[O:22])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 22285400Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

Product 1

HCID 22285629Ethyl 3-cyclopropyl-2-oxopropanoate

Procedure

A fifth aspect of this invention is a process for the preparation of ethyl 3-cyclopropyl-2,2-difluoropropanoate, which process comprises: (a) reacting bromomethylcyclopropane with 2-carboethoxy-1,3-dithiane in the presence of strong base to give ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate; (b) reacting the ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate with N-bromosuccinimide to give ethyl 3-cyclopropyl-2-oxopropanoate; and (c) reacting the ethyl 3-cyclopropyl-2-oxopropanoate with a fluorinating agent.

Sources & evidence

ORD record
ord-427d786cfb2f4163af2f24387f3ed683
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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