Bromoacetyl bromide → HCID 86649653, compound

HRID 2367852Notes

Reaction equation

HRID 2367852 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:4].Br[CH2:16][C:17](Br)=[O:18].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[C:17]([C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([F:13])([F:14])[F:1])=[C:7]([CH3:12])[CH:8]=1)(=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 137696Acetamide, 2,2,2-trifluoro-N-(2-methylphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 86649653HCID 86649653, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2,2,2-trifluoro-N-o-tolylacetamide (8.0 g; 39.4 mmol) was dissolved in 20 mL CS2. Bromoacetic bromide (8.4 g; 68.3 mmol) was added dropwise. AlCl3 (16.0 g; 120 mmol) was added in portions, with drying tube attached to the reaction flask. The reaction mixture was refluxed overnight. After reaction, the solvent was removed. Ice and water were added, and some yellow solid precipitated. The solid was isolated by filtration, and purified by silica gel column chromatography, to afford 3.8 g (yield 39%) of product as off-white solid. 1H NMR (300 MHz; CDCl3), δ 8.30 (s, 1H, Ar—H), 7.91 (brs, 1H, NH), 7.81 (d, 3JHH=8.2 Hz, 1H, Ar—H), 7.36 (d, 3JHH=7.9 Hz, 1H, Ar—H), 2.60 (s, 3H, COCH3), 2.36 (s, 3H, CH3).

Workup

  1. customwith drying tube
  2. temperatureThe reaction mixture was refluxed overnight
  3. customAfter reaction
  4. customthe solvent was removed
  5. additionIce and water were added
  6. customsome yellow solid precipitated
  7. customThe solid was isolated by filtration
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f36302fa9a94887a37ccc28c3a0e50a
Source dataset
uspto-grants-2014_04
Patent number
US08703096B2

Reaction notes

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