N-bromobutanimide → 12-bromo-2,10-dichloro-12H-5,7-dioxadibenzo[a,d]cyclooctene
Reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1.[Br:19]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:19][CH:11]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[O:6][CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:10]1=2Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2,10-dichloro-12H-dibenzo[d,g][1,3]-dioxocin (21.4 g, 76.1 mmol) and N -bromosuccinimide (13.5 g, 76.1 mmol) in tetrachloromethane (275 mL) was added azo-bisisobutyronitrile (200 mg, 1.2 mmol). The mixture was heated at 80° C. for 24 h. Another 3×azobisisobutyronitrile (200 mg, 1.2 mmol) was added within the 24 h. The mixture was filtrated and the solution phase concentrated in vacuo. The residue was added dichloromethane (30 mL) and ether (100 mL). The mixture was filtered and the solution phase concentrated in vacuo. The residue was submitted to flash chromatography eluting with heptane/ethyl acetate (3:1) to give 7.4 g (27%) of 12-bromo-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene.
Workup
- filtrationThe mixture was filtrated
- concentrationthe solution phase concentrated in vacuo
- additionThe residue was added dichloromethane (30 mL) and ether (100 mL)
- filtrationThe mixture was filtered
- concentrationthe solution phase concentrated in vacuo
- washeluting with heptane/ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-754a85b7e2c14ec0a09707896ee8ebd8
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723731B2
Reaction notes
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