2-Bromo-4'-(trifluoromethyl)acetophenone → HCID 22147881, compound

HRID 2114950Notes

Reaction equation

HRID 2114950 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].[F:10][C:11]([F:23])([F:22])[C:12]1[CH:21]=[CH:20][C:15]([C:16](=O)[CH2:17]Br)=[CH:14][CH:13]=1>>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:8][CH:17]=[C:16]([C:15]2[CH:20]=[CH:21][C:12]([C:11]([F:10])([F:22])[F:23])=[CH:13][CH:14]=2)[N:9]=1

Participants

3

Reactant 2

HCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 28080883-chlorothiophene-2-carboxamide

Product 1

HCID 22147881HCID 22147881, compoundYield 6%

Conditions

Temperature
150 °C

Procedure

3-Chloro-thiophene-2-carboxamide (0.145 g, 0.898 mmol) and 4-trifluoromethyl-phenacyl bromide (0.200 g, 0.749 mmol) were placed in a sealed tube and heated at 150° C. for 4 h. The reaction mixture was quenched with ethyl acetate and the residue was purified by column chromatography (gradient 100:1, 20:1 hexane:dichloromethane). The product was further purified by preparative-TLC (100:1, hexane:dichloromethane) to yield 0.0148 g (5.0%) of the title compound as a white solid. 1H NMR (Acetone-d6): 8.58 (s, 1H), 8.01 (d, J=8.1 Hz, 2H), 7.71 (t, 3H), 7.10 (d, J=5.1 Hz, 1H), 7.08 (d, J=5.7 Hz, 1H).

Workup

  1. customThe reaction mixture was quenched with ethyl acetate
  2. customthe residue was purified by column chromatography (gradient 100:1, 20:1 hexane:dichloromethane)
  3. customThe product was further purified by preparative-TLC (100:1, hexane:dichloromethane)

Sources & evidence

ORD record
ord-b3e292a3523b45368032c1556e3e8258
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

Loading…