Benzyl Bromide → HCID 58340821, compound
Reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][NH:10][C:9]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:10]1[C:9]2[CH:14]=[C:5]([CH2:4][C:3]3[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:2]=3[Br:1])[CH:6]=[CH:7][C:8]=2[O:13][CH2:12][CH2:11]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 6-(2-bromo-5-iodo-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (9.4 g, 21.86 mmol) in DMF (50 mL) was added potassium carbonate (6.04 g, 43.71 mmol), benzyl bromide (3.2 mL, 26.23 mmol) and the mixture was heated to 50° C. overnight. The reaction mixture was cooled to room temperature, quenched by the addition of water (100 mL), then extracted with ethyl acetate (3×50 mL). The organic layers were combined then washed with water (50 mL), brine (50 mL), dried over sodium sulfate, and concentrated to a residue which was purified by silica gel column chromatography to furnish 4-benzyl-6-(2-bromo-5-iodo-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (10.5 g).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customquenched by the addition of water (100 mL)
- extractionextracted with ethyl acetate (3×50 mL)
- washThe organic layers were combined then washed with water (50 mL), brine (50 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated to a residue which
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-10de936478614e898c96606c2b86490f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828951B2
Reaction notes
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