Tetrahydrofuran → 1,2-Benzisoxazole, 6-bromo-3-(trifluoromethyl)-

HRID 1400012Notes

Reaction equation

HRID 1400012 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:13][OH:14])[C:9]([F:12])([F:11])[F:10])=[C:4](F)[CH:3]=1.N12CCCN=C1CCCCC2.C1COCC1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]([C:9]([F:12])([F:11])[F:10])=[N:13][O:14][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866351391-(4-Bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanone oxime

Product 1

HCID 669581861,2-Benzisoxazole, 6-bromo-3-(trifluoromethyl)-Yield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A solution consisting of 1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanone oxime (3.2 g, 11 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.1 mL, 7.4 mmol) and THF (42 mL) was heated at 150° C. via microwave irradiation for 30 min. The reaction mixture was diluted with CH2Cl2 (25 mL) and washed with HCl (1 N aq., 25 mL). The organic layer was then dried (Na2SO4), concentrated and purified (FCC) to yield the title compound (1.97 g, 66%).

Workup

  1. washwashed with HCl (1 N aq., 25 mL)
  2. dry with materialThe organic layer was then dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified (FCC)

Sources & evidence

ORD record
ord-1233bc12bf504ff08f4d17e39c76578c
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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