3-(Trifluoromethyl)aniline → 2,5-Dimethyl-N-[3-(trifluoromethyl)phenyl]aniline

HRID 2266976Notes

Reaction equation

HRID 2266976 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH3:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[NH:15][C:14]1[CH:16]=[CH:17][CH:18]=[C:12]([C:11]([F:10])([F:19])[F:20])[CH:13]=1

Participants

5

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 8909Butyl etherHCID 32883Chloro-p-xyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 578574872,5-Dimethyl-N-[3-(trifluoromethyl)phenyl]anilineYield 94%

Conditions

Temperature
110 °C

Procedure

Following general procedure E, a mixture of 2-chloro-p-xylene (134 μL, 1.0 mmol), 3-(trifluoromethyl)aniline (150 μL, 1.2 mmol), NaOt-Bu (115 mg, 1.2 mmol), 10 (0.08 mg, 0.01 mol %), 1 (0.05 mg, 0.01 mol %), and Bu2O (1 mL) was heated to 110° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a clear oil (248 mg, 94%). 1H NMR (300 MHz, CDCl3) δ: 7.38 (t, J=8.0 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.16 (m, 3H), 7.08 (d, J=8.0 Hz, 1H), 6.95 (d, J=8.0 Hz, 1H), 5.53 (s, 1H), 2.39 (s, 3H), 2.28 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 145.5, 139.8, 137.1, 132.6, 132.2, 131.8, 131.8, 131.4, 130.1, 130.0, 127.5, 126.4, 124.9, 124.9, 124.8, 122.8, 122.1, 122.0, 119.2, 119.1, 116.3, 116.3, 112.8, 21.4, 17.7 ppm. IR (neat, cm−1): 3391, 3021, 2924, 1613, 1485, 1337, 1165, 1124, 787, 699. Anal. Calcd. for C15H14F3N: C, 67.91; H, 5.32. Found: C, 68.02; H, 5.31.

Workup

  1. customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-22139aa55e004e909965fff733b2a2b2
Source dataset
uspto-grants-2010_12
Patent number
US07858784B2

Reaction notes

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