Bromomethylcyclopropane → Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

HRID 2190953Notes

Reaction equation

HRID 2190953 reaction equation
[CH:1]1([CH2:4][C:5](F)(F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.BrCC1CC1.C(C1[S:28][CH2:27][CH2:26][CH2:25][S:24]1)(OCC)=O>>[CH:1]1([CH2:4][C:5]2([C:6]([O:8][CH2:9][CH3:10])=[O:7])[S:28][CH2:27][CH2:26][CH2:25][S:24]2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 88552Ethyl 1,3-dithiane-2-carboxylateHCID 50997080Ethyl 3-cyclopropyl-2,2-difluoropropanoate

Product 1

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

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-b927b6e496554bd88b463251483c9cbd
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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