Bromoacetyl bromide → HCID 17759202, compound

HRID 2367854Notes

Reaction equation

HRID 2367854 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:15][CH2:16][C:17](Br)=[O:18].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[Br:15][CH2:16][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]

Participants

5

Reactant 3

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

Product 1

HCID 17759202HCID 17759202, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2,2,2-trifluoro-N-o-tolylacetamide (5.0 g; 24.6 mmol) was dissolved in 20 mL CS2. The mixture was cooled below 10° C. Bromoacetic bromide (10.1 g; 50.0 mmol) was added dropwise. AlCl3 (10.0 g; 75.0 mmol) was added in portions, with drying tube attached to the reaction flask. The reaction mixture was refluxed overnight. After the reaction is complete as monitored by TLC, the upper CS2 layer was removed. The lower layer was added into 7.0 mL ice water mixed with HCl. The product was extracted into CH2Cl2, and dried over MgSO4. The solvent was removed, and the solid was dried to afford 5.0 g of crude product, which was purified by silica gel column chromatography, to afford 3.0 g (yield 38%) of product as yellow solid. 1H NMR (300 MHz; CDCl3), δ 8.40 (s, 1H, Ar—H), 7.87 (brs+d, 3JHH=8.0 Hz, 2H, Ar—H), 7.43 (d, 3JHH=8.0 Hz, 1H, Ar—H), 4.46 (s, 2H, COCH2Br), 2.41 (s, 3H, CH3).

Workup

  1. temperatureThe mixture was cooled below 10° C
  2. customwith drying tube
  3. temperatureThe reaction mixture was refluxed overnight
  4. customthe upper CS2 layer was removed
  5. additionThe lower layer was added into 7.0 mL ice water
  6. additionmixed with HCl
  7. extractionThe product was extracted into CH2Cl2
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed
  10. customthe solid was dried
  11. customto afford 5.0 g of crude product, which
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7b77b412831d40738708f439b6b6bcd1
Source dataset
uspto-grants-2014_04
Patent number
US08703096B2

Reaction notes

Loading…