Dichloromethane → HCID 136167104, compound

HRID 1888709Notes

Reaction equation

HRID 1888709 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[N:8][O:9][C:5]=2[CH:4]=1.C(Cl)Cl.B(Br)(Br)Br.C(Cl)Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[N:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 22277759Boron tribromide dichloromethane2×HCID 58047331HCID 58047331, compound

Product 1

HCID 136167104HCID 136167104, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-[1-(6-methoxy-1,2-benzisoxazol-3-yl)ethyl]acetamide (500 mg, 2.13 mmol) obtained in Reference Example 9 in toluene (10 mL) was added 1 M boron tribromide methylene chloride solution (6.40 mL, 6.40 mmol) under ice-cooling and, under a nitrogen atmosphere, the mixture was stirred at room temperature for 1 hr. Methylene chloride (5 mL) and 1 M boron tribromide methylene chloride solution (5.00 mL, 5.00 mmol) were added thereto at room temperature, and the mixture was stirred under heating at 50° C. for 16 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (470 mg, quantitative) as an oil. This was used for the next step without purification.

Workup

  1. temperaturecooling and, under a nitrogen atmosphere
  2. stirringat room temperature, and the mixture was stirred
  3. temperatureunder heating at 50° C. for 16 hr
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-692284e77b58450d8b3a2b038a470555
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…