3-Bromothiophene-2-carbonitrile → 3-(2-Fluoro-5-nitrophenyl)thiophene-2-carbonitrile

HRID 2184000Notes

Reaction equation

HRID 2184000 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]#[N:8].[F:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]#[N:8]

Participants

3

Reactant 2

HCID 27400883-Bromothiophene-2-carbonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 224735433-(2-Fluoro-5-nitrophenyl)thiophene-2-carbonitrile

Procedure

3-Bromothiophene-2-carbonitrile was coupled with 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane using the conditions described in Example 1 to give 3-(2-fluoro-5-nitrophenyl)thiophene-2-carbonitrile as an off-white solid. This in turn was reduced using the conditions outlined in Example 1 to give 3-(5-amino-2-fluorophenyl)thiophene-2-carbonitrile: δH (400 MHz, CDCl3) 3.67 (2H, s), 6.68-6.72 (1H, m), 6.90 (1H, dd, J 6 and 3), 7.00 (1H, dd, J 9 and 1), 7.30 (1H), dd, J 5 and 2), 7.60 (1H, d, J 5).

Sources & evidence

ORD record
ord-9ee982c2189e412d9fc659d41fd614d4
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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