Azobisisobutyronitrile → 3-Bromo-6-(trifluoromethyl)phthalide
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][C:9]2=[O:12])=[CH:5][CH:4]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:22][CH:7]1[C:6]2[C:10](=[CH:11][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:4][CH:5]=2)[C:9](=[O:12])[O:8]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Into a 50 mL round-bottom flask, was placed a solution of 6-(trifluoromethyl)isobenzofuran-1(3H)-one (prepared as described in the previous step, 5.5 g, 27.23 mmol, 1.00 equiv) in CCl4 (10 mL), NBS (5.8 g, 32.58 mmol, 1.20 equiv) and AIBN (0.45 g, 0.10 equiv). The reaction mixture was stirred for 3 h at 65° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in 100 mL of ethyl acetate, washed with 60 mL of brine, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow oil.
Workup
- customInto a 50 mL round-bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- dissolutionThe residue was dissolved in 100 mL of ethyl acetate
- washwashed with 60 mL of brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-1e4376fe6a214490ac0716150eb605a3
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062048B2
Reaction notes
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