Potassium Iodide → 2-(4-bromophenoxy)-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

HRID 1809153Notes

Reaction equation

HRID 1809153 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=1)=[O:12].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:22])[F:23])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 10476772-(4-bromophenoxy)-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamideYield 94.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask was added 4-bromophenol (1.7 g, 9.8 mmol, 1.0 eq.), acetamide 21 (2.79 g, 10.3 mmol, 1.05 eq.), potassium iodide (1.7 g, 10.3 mmol, 1.05 eq.), potassium carbonate (2.7 g, 19.6 mmol, 2.0 eq.), and acetonitrile (35.0 mL). The reaction mixture was then reluxed with vigorous stirring for 2 h. The hot reaction was then filtered to remove the insoluble potassium carbonate. The filtrate was concentrated to give 3.8 g of crude bromo-phenoxy-acetamide 22 as a light brown solid. The solid was then triturated with 10 mL of cold acetonitrile, filtered, and rinsed with 5 mL of cold acetonitrile to give pure bromo-phenoxy-acetamide 22 (1.85 g, 45% yield). Note: there was still an abundant amount of crude product in the mother liquor. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 409.9 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 8.20 (d, 1H), 7.90 (dd, 1H), 7.68 (d, 1H), 7.48 (d, 2H), 6.99 (d, 2H), 4.75 (s, 2H) ppm.

Workup

  1. customThe hot reaction
  2. filtrationwas then filtered
  3. customto remove the insoluble potassium carbonate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-22f9b0711c3746b3aac8c1f555531886
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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