2-Bromopyridine → 2-(2-Fluorophenyl)pyridine

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O>>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 27343542-Fluorophenylboronic acid

Product 1

HCID 98555982-(2-Fluorophenyl)pyridine

Procedure

2-Bromopyridine and 2-fluorobenzeneboronic acid were coupled using the procedure described in Example 43 to afford 2-(2-fluorophenyl)pyridine as a pale yellow oil which crystallised on standing: δH (400 MHz, CDCl3) 7.13-7.19 (1H, m), 7.24-7.28 (2H, m), 7.35-7.41 (1H, m), 7.73-7.81 (2H, m), 7.97 (1H, ddd, J 8, 8 and 2), 8.72-8.74 (1H, m); m/z (ES+) 174 (M++H).

Sources & evidence

ORD record: ord-0be55537559a4ef2bb039ad2cbd0a3fa
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

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