4-Chloropyridine hydrochloride → 4-Chloro-2-cyclopropylpyridine

HRID 1430151Notes

Reaction equation

HRID 1430151 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Cl.[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH:1]2[CH2:2][CH2:3]2)[CH:9]=1

Participants

4

Reactant 2

HCID 818524-Chloropyridine hydrochlorideHCID 178418630HCID 178418630, compound

Product 1

HCID 592936784-Chloro-2-cyclopropylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared according to a modification of a procedure described in the literature [Comins, D. L.; Mantlo, N. B., Journal of Organic Chemistry, (1985), 50, 4410-4411]. Cyclopropylmagnesium bromide (0.5M in THF, 100 mL, 50 mmol, 2.2 eq) is added in one portion to a cold (−78° C.) suspension of 4-chloropyridine hydrochloride (3.4 g, 22 mmol) in THF (68 mL).

Sources & evidence

ORD record
ord-00b6ea2f60914a5c8c547722476ca72c
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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