3,4-Difluoroaniline → HCID 86709746, compound

HRID 2174613Notes

Reaction equation

HRID 2174613 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4]([C:5]2[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2)[C@@H:3]1[C:12]([OH:14])=O.[F:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[F:24])[NH2:20]>>[F:16][C:17]1[CH:18]=[C:19]([NH:20][C:12]([C@H:3]2[C@H:4]([C:5]3[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=3)[C:2]2([CH3:1])[CH3:15])=[O:14])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

3

Reactant 2

HCID 774693,4-DifluoroanilineHCID 86709747HCID 86709747, compound

Product 1

HCID 86709746HCID 86709746, compoundYield 92%

Procedure

trans-2,2-Dimethyl-3-m-tolyl-cyclopropanecarboxylic acid (2.04 g, 10 mmol) and 3,4-difluoroaniline (1.29 g, 10 mmol) were reacted as described under General Procedure D to furnish the title compound (2.9 g, 92%) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 7.70-7.64 (m, 1H), 7.47 (s, 1H), 7.20-6.96 (m, 6H), 2.79 (d, J=5.6 Hz, 1H), 2.33 (s, 3H), 1.80 (d, J=5.6 Hz, 1H), 1.40 (s, 3H), 0.97 (s, 3H). mp 110-113° C. ESIMS m/z [M+H]+ 316.2.

Sources & evidence

ORD record
ord-16b1fe3cd4f645c9be1e62567e519748
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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