4-Bromo-2-methyl-6-nitroaniline → 2'-Fluoro-5-methyl-biphenyl-3,4-diamine

HRID 1518154Notes

Reaction equation

HRID 1518154 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH2:11])=[C:4]([CH3:12])[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B1OC(C)(C)C(C)(C)O1>>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([NH2:11])=[C:6]([NH2:8])[CH:7]=1

Participants

3

Reactant 2

HCID 5226794-Bromo-2-methyl-6-nitroanilineHCID 121597222-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 592801102'-Fluoro-5-methyl-biphenyl-3,4-diamine

Procedure

The title compound was prepared from 4-bromo-2-methyl-6-nitro-phenylamine and 2-(2-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane using the procedures described in Example 1, steps D and E. 1H-NMR (400 MHz, CDCl3) δ: 7.36 (td, J=7.8, 1.9 Hz, 1H), 7.16-7.23 (m, 1H), 7.03-7.15 (m, 2H), 6.84 (s, 1H), 6.79-6.82 (m, 1H), 3.47 (br. s., 4H), 2.20 (s, 3H).

Sources & evidence

ORD record
ord-3df858fd05e64266b4e74258b4fc0147
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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