Hydrogen Bromide → 4-(4-Bromophenyl)oxane
Reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10](N)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.N([O-])=O.[Na+].[BrH:18]>O>[Br:18][C:10]1[CH:11]=[CH:12][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:8][CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
A solution of 4-(tetrahydro-2H-pyran-4-yl)benzenamine (1.79 g, 10.10 mmol) in 15 mL of HBr and 5 mL of water was stirred at 0° C. for 10 minutes, then 0.77 g of NaNO2 was added to the mixture at −5° C.˜0° C. The mixture was stirred at −5° C. for 30 minutes. Then the solution of CuBr in 3 mL of HBr was added to the mixture, after that the mixture was heated at 100° C. for 2 hours. The mixture was cooled to room temperature, partitioned between 2N NaOH and EA, washed with water and aqueous NaCl, dried over Na2SO4. The volatiles were removed in vacuo, and the residue was purified by chromatography with PE/EA (10:1˜4:1) to give 1.11 g of title compound.
Workup
- temperatureafter that the mixture was heated at 100° C. for 2 hours
- temperatureThe mixture was cooled to room temperature
- custompartitioned between 2N NaOH and EA
- washwashed with water and aqueous NaCl
- dry with materialdried over Na2SO4
- customThe volatiles were removed in vacuo
- customthe residue was purified by chromatography with PE/EA (10:1˜4:1)
Sources & evidence
- ORD record
- ord-dcce06dea5894c04813cf9863827b506
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434726B2
Reaction notes
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