1-Bromo-2,6-difluorobenzene → 2',6'-Difluoro-5-methyl-biphenyl-3,4-diamine

HRID 1518152Notes

Reaction equation

HRID 1518152 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[N+:18]([O-])=O.Br[C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1[F:29]>>[F:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:29])[C:22]=1[C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([NH2:1])=[C:3]([NH2:18])[CH:4]=1

Participants

3

Reactant 2

HCID 1235571-Bromo-2,6-difluorobenzeneHCID 251301272-Methyl-6-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 592800862',6'-Difluoro-5-methyl-biphenyl-3,4-diamine

Procedure

The title compound was prepared from 2-methyl-6-nitro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (as prepared in Example 8, step A) and 2-bromo-1,3-difluoro-benzene according to the procedures described in Example 4, step A and Example 1, step E. 1H-NMR (400 MHz, CDCl3) δ: 7.17 (tt, J=8.3, 6.3 Hz, 1H), 6.87-6.97 (m, 2H), 6.76 (s, 1H), 6.72 (s, 1H), 3.44 (br. s., 4H), 2.21 (s, 3H).

Sources & evidence

ORD record
ord-408a4cada5574982b55c40b9c8755511
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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