3-Chloro-4-fluoroaniline → HCID 88532935, compound

HRID 1529828Notes

Reaction equation

HRID 1529828 reaction equation
Cl[C:2]1[C:7]2[Se:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:6]=2[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[F:23])[NH2:19].[K+].[Br-]>C(O)(C)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:4]2[N:3]=[CH:2][C:7]3[Se:8][C:9]4[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=4[C:6]=3[N:5]=2)[CH:20]=[CH:21][C:22]=1[F:23]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 253877Potassium BromideHCID 88533012HCID 88533012, compound

Product 1

HCID 88532935HCID 88532935, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of step c compound (700 mg, 2.57 mmol) in isopropanol (15 mL) was added 3-chloro-4-fluoroaniline (1.6 g, 11.56 mmol) at rt and the mixture was refluxed for 1.5 h. Work-up of the mixture as described in example 1, gave the product as an off-white color solid, mp 238-240° C. IR (KBr) νmax cm−1; 1H NMR (400 MHz, CDCl3): δ 8.71 (1H, s), 7.70 (1H, dd, J=6.4, 2.8 Hz), 7.37-7.41 (1H, m), 7.16 (1H, t, J=8.8 Hz), 6.53 (1H, br s, exchangeable with D2O), 2.92 (2H, t, J=6.0 Hz), 2.82 (2H, t, J=6.0 Hz), 1.86-1.99 (4H, m); 13C NMR (100 MHz, DMSO-d6): δ 162.5, 156.2, 153.8, 153.0 (d, J=241 Hz), 148.6, 136.9 (d, J=3.0 Hz), 133.1, 122.7, 121.6 (d, J=7.0 Hz), 118.8 (d, J=19 Hz), 116.5 (d, J=21.0 Hz), 115.6, 27.6, 24.4, 23.5, 21.3; LC-MS (negative ion mode): m/z 378, 380, 382 (M−H)−.

Workup

  1. temperaturethe mixture was refluxed for 1.5 h
  2. customgave the product as an off-white color solid, mp 238-240° C

Sources & evidence

ORD record
ord-f15b622b209d47a8b034d56a46f74032
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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