2-Bromo-3-fluorobenzotrifluoride → HCID 50994194, compound

HRID 1518132Notes

Reaction equation

HRID 1518132 reaction equation
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[F:12].[NH2:13][C:14]1[CH:19]=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][C:15]=1[N+:29]([O-:31])=[O:30]>>[F:12][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]=1[C:17]1[CH:18]=[CH:19][C:14]([NH2:13])=[C:15]([N+:29]([O-:31])=[O:30])[CH:16]=1

Participants

3

Reactant 2

HCID 5178472-Bromo-3-fluorobenzotrifluorideHCID 162179142-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 50994194HCID 50994194, compoundYield 89%

Procedure

Using the procedure for step A in Example 4, the title compound was prepared from 1-bromo-2-fluoro-6-trifluoromethylbenzene (0.850 mL, 6.09 mmol) and 4-amino-3-nitrophenylboronic acid pinacol ester (1.3 eq., 2.09 g, 7.92 mmol) in 89% yield (1.62 g). 1H-NMR (400 MHz, CDCl3) δ: 8.10 (s, 1H), 7.53-7.61 (m, 1H), 7.43-7.53 (m, 1H), 7.35 (t, J=8.5 Hz, 1H), 7.30 (d, J=7.3 Hz, 1H), 6.89 (d, J=8.3 Hz, 1H), 5.47 (br. s., 2H).

Sources & evidence

ORD record
ord-2dbe7ef60b4f4d189cad63ec1eb52e8a
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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