Diethyl Ether → HCID 59232175, compound

HRID 1099266Notes

Reaction equation

HRID 1099266 reaction equation
[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[N:22]=[C:23]=[O:24].CCOCC>C1COCC1>[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH:6][C:23]([NH:22][C:13]2[CH:14]=[C:15]([C:18]([F:19])([F:21])[F:20])[CH:16]=[CH:17][C:12]=2[F:11])=[O:24])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 70180404-Bromo-2-fluoro-5-methylaniline

Product 1

HCID 59232175HCID 59232175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-2-fluoro-5-methylaniline (500 mg, 2.45 mmoL) in THF (3 mL) was added the 2-fluoro-5-(trifluoromethyl)phenyl isocyanate (625 mg, 3.0 mmol). The reaction generated a white solid within 10 min. An additional portion of THF (3 mL) was added and the mixture dissolved. TLC analysis (1:1 Et2O:Hex) indicated that the reaction was complete. The product was purified by flash column chromatography (Hex:Et2O 2:1 to Et2O). 1H-NMR (DMSO-d6) δ 9.37 (d, J=2.8 Hz, 1H), 9.17 (d, J=2.4 Hz, 1H), 8.61 (dd, J=7.2, 2 Hz, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.55 (d, J=10.8 Hz, 1H), 7.49 (dd, J=10.8, 8.8 Hz, 2H), 7.39 (m, 1H), 2.29 (s, 3H); MS [M+H]+=409.3, LCMS RT=3.91 min.

Workup

  1. customwithin 10 min
  2. dissolutionthe mixture dissolved
  3. customThe product was purified by flash column chromatography (Hex:Et2O 2:1 to Et2O)

Sources & evidence

ORD record
ord-421cb8d6bb604e66b7cc04197673bdb2
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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