Bromine → HCID 10615399, compound

HRID 326591Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.C([O-])(=O)C.[Na+].[Br:24]Br>CO>[Br:24][C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:18])([CH3:1])[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:5]=2[CH:14]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Methanol (25 ml) was added to a mixture of Compound 2 (1.19 g) and sodium acetate (0.82 g). The mixture was cooled to -40° C. and bromine (0.96 g) was added to the mixture. After completion of the addition, the mixture was warmed and the mixture was stirred at 5° to 8° C. for 18 hours. The reaction was quenched by adding aqueous sodium sulfite solution, and the methanol was distilled off. The residue was extracted with ethyl acetate. The extract was successively washed with aqueous sodium bicarbonate solution and saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate/hexane to obtain 6-bromo-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.41 g) (Compound 4).

Workup

additionAfter completion of the addition
temperaturethe mixture was warmed
customThe reaction was quenched
additionby adding aqueous sodium sulfite solution
distillationthe methanol was distilled off
extractionThe residue was extracted with ethyl acetate
washThe extract was successively washed with aqueous sodium bicarbonate solution and saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off
washeluted with ethyl acetate/hexane

Sources & evidence

ORD record: ord-07eabd6ff4c74a5d8929f98471158c5a
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270308

Reaction notes

Loading…