1,2-Dibromoethane → 1-(6-Bromopyridin-2-YL)cyclopropane-1-carboxylic acid

Reaction equation

C([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)C.Br[CH2:15][CH2:16]Br>>[Br:12][C:8]1[N:7]=[C:6]([C:5]2([C:4]([OH:3])=[O:13])[CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 78391,2-Dibromoethane

HCID 53419420Ethyl 2-(6-bromopyridin-2-yl)acetate

Product 1

HCID 722119951-(6-Bromopyridin-2-YL)cyclopropane-1-carboxylic acidYield 57%

Procedure

The title compound was prepared from (6-bromo-pyridin-2-yl)-acetic acid ethyl ester and 1,2-dibromoethane following a procedure analogous to that described in Step 3 for Intermediate 4; under these conditions the ester group was hydrolyzed. Yield: 57% of theory; LC (method 3): tR=2.60 min; Mass spectrum (ESI+): m/z=242/244 (Br) [M+H]+.

Sources & evidence

ORD record: ord-8a41f52ea8354164931c5bdd93017cb9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090605B2

Reaction notes

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