1,2-Dibromoethane → 9-Bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 1629067Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)=[C:6]([OH:8])[CH:7]=1.Br[CH2:15][CH2:16]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[N:13]([CH:12]=[CH:11][N:10]=3)[CH2:15][CH2:16][O:8][C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-(1H-imidazol-2-yl)phenol (0.9 g, 4 mmol), 1,2-dibromoethane (1.3 mL, 15 mmol) and cesium carbonate (4.9 g, 15 mmol) in DMF (20 mL) was heated to 90° C. for 12 h. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with water, brine and dried over MgSO4 and concentrated to give 9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (0.8 g).

Workup

customThe mixture was partitioned between water and ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-f955c51c8bd34caf99d91427a2de7945
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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