2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 28839372, compound

HRID 2281240Notes

Reaction equation

HRID 2281240 reaction equation
[NH2:1][C:2](=[S:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O>C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:1]=[C:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[S:9][CH:11]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2771567ethyl 3-amino-3-thioxopropanoate

Product 1

HCID 28839372HCID 28839372, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 3-amino-3-thioxopropanoate (20.00 g, 135.9 mmol) in ethanol (120 mL) was added 2-bromo-4′-fluoroacetophenone (29.49 g, 135.9 mmol). The mixture was refluxed for 1 hour, concentrated and partitioned between ethyl acetate (300 mL) and aqueous NaHCO3 (400 mL). The organic layer was combined with a backextract of the aqueous layer (ethyl acetate, 1×100 mL), dried (Na2SO4) and concentrated. The resulting light brown solid was purified by flash chromatography using a hexane/ethyl acetate gradient to afford ethyl 2-(4-(4-fluorophenyl)thiazol-2-yl)acetate as an off-white solid (29.92 g, 83%).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate (300 mL) and aqueous NaHCO3 (400 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting light brown solid was purified by flash chromatography

Sources & evidence

ORD record
ord-e4025cd443904082b34635f01eac6aa9
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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