N-bromobutanimide → cis-4-[4-Bromo-3-(2-methyl-3-furanyl)phenyl]-2,6-dimethylmorpholine

HRID 2278429Notes

Reaction equation

HRID 2278429 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]1[O:15][C@@H:14]([CH3:16])[CH2:13][N:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][O:25][C:24]=3[CH3:28])[CH:18]=2)[CH2:11]1>C(Cl)(Cl)Cl>[Br:1][C:20]1[CH:21]=[CH:22][C:17]([N:12]2[CH2:11][C@H:10]([CH3:9])[O:15][C@H:14]([CH3:16])[CH2:13]2)=[CH:18][C:19]=1[C:23]1[CH:27]=[CH:26][O:25][C:24]=1[CH3:28]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67513891cis-2,6-Dimethyl-4-[3-(2-methyl-3-furanyl)phenyl]morpholine

Product 1

HCID 69088074cis-4-[4-Bromo-3-(2-methyl-3-furanyl)phenyl]-2,6-dimethylmorpholine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (380 mg, 2.137 mmol) was added portionwise to a solution of cis-2,6-dimethyl-4-[3-(2-methyl-3-furanyl)phenyl]morpholine (580 mg, 2.137 mmol) in chloroform (10 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. Crude LC/MS showed desired product can be seen and no starting material left, so the reaction mixture was diluted with ethyl acetate and washed with water, brine, water and brine. The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure.

Sources & evidence

ORD record
ord-204d74eb663d4fe9b744762f9f63fd41
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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