Sulfuric Acid → HCID 68386631, compound

HRID 1522764Notes

Reaction equation

HRID 1522764 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11][N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](B(CC)CC)[CH3:27].S(=O)(=O)(O)O>CN(C=O)C.C(Cl)Cl.O>[CH2:26]([C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11][N:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1)[CH3:27]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 68387186HCID 68387186, compound

Product 1

HCID 68386631HCID 68386631, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 3-(3-bromo-5-fluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate (1000 mg, 3.03 mmol), potassium carbonate (1.67 g, 12.12 mmol) and tetrakis(triphenylphosphane)palladium (350 mg, 0.30 mmol) were suspended in DMF (10 ml). Triethylborane (1M in hexane, 4.24 ml, 4.24 mmol) was then added, and the reaction mixture was heated in a microwave oven at 150° C. for 30 min. After cooling, water (20 ml), sulfuric acid (1 M, 5 ml) and CH2Cl2 (20 ml) were added, and the mixture was shaken. The organic phase was then dried over Na2SO4, and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel using the mobile phase heptane/EtOAc gave 701 mg (83%) of ethyl 3-(3-ethyl-5-fluorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate.

Workup

  1. temperatureAfter cooling
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3f80768b455a49e0aae8cc30a1d78d63
Source dataset
uspto-grants-2015_07
Patent number
US09078442B2

Reaction notes

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