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

HRID 1518156Notes

Reaction equation

HRID 1518156 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.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])O1>>[CH3:12][C:4]1[C:5]([NH2:11])=[C:6]([NH2:8])[CH:7]=[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH:3]=1

Participants

3

Reactant 2

HCID 5226794-Bromo-2-methyl-6-nitroanilineHCID 177502822-(2-(Trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 592800585-Methyl-2'-trifluoromethyl-biphenyl-3,4-diamine

Procedure

The title compound was prepared from 4-bromo-2-methyl-6-nitro-phenylamine and 4,4,5,5-tetramethyl-2-(2-trifluoromethyl-phenyl)-[1,3,2]dioxaborolane according to the procedures described in Example 1, steps D and E. 1H-NMR (400 MHz, CDCl3) δ: 7.68 (d, J=7.8 Hz, 1H), 7.47 (t, J=7.3 Hz, 1H), 7.36 (t, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 6.59 (s, 1H), 6.61 (s, 1H), 3.41 (br. s., 4H), 2.19 (s, 3H).

Sources & evidence

ORD record
ord-0c4d04fdb8264032b8182457b89c9e43
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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