Ethyl 4-bromobutyrate → Ethyl 4-(2-fluoroimidazol-1-yl)butyrate

Reaction equation

Cl.[F:2][C:3]1[NH:4][CH:5]=[CH:6][N:7]=1.Br[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[F:2][C:3]1[N:4]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][N:7]=1

Participants

Reactant 2

HCID 76300Ethyl 4-bromobutyrate

HCID 126246272-Fluoro-1H-imidazole hydrochloride

Product 1

HCID 20432450Ethyl 4-(2-fluoroimidazol-1-yl)butyrate

Procedure

Using the technique for the starting material of Example 74, 2-fluoroimidazole hydrochloride was alkylated with ethyl 4-bromobutyrate to give ethyl 4-(2-fluoroimidazol-1-yl)butyrate, having the following n.m.r. in CDCl3 : 1.3 (t, 3H); 1.9-2.5 (m, 4H); 3.9 (t, 2H); 4.1 (q, 2H); 6.5 (d, 1H); 6.6 (d, 1H).

Sources & evidence

ORD record: ord-f45940424df042e48a886e1c906b8843
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492692

Reaction notes

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