Dimethyl Sulfate → 9-Bromo-1-methyl-1,10-phenanthrolinium hydrogen sulfate

HRID 716558

Reaction equation

[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.[S:16]([O:21]C)([O:19][CH3:20])(=[O:18])=[O:17]>C(OCC)C>[S:16]([O-:21])([OH:19])(=[O:18])=[O:17].[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4]([N:3]=1)=[C:5]1[C:10]([CH:9]=[CH:8][CH:7]=[N+:6]1[CH3:20])=[CH:11][CH:12]=2

Participants

Conditions

Temperature: 120 °C

Procedure

Under a stream of argon, to compound (7) (24.4 g; 94.2 mmol), dimethyl sulfate (77 g; 610 mmol) was added in an ice bath over 20 minutes. The reaction temperature was raised to 120° C. and the resulting reaction mixture was stirred for 1 hour. To the reaction mixture, diethyl ether was added in an ice bath, and solids which precipitated out were separated by filtration. The resulting solids were washed with a mixed solution of diethyl ether/ethanol (1/1 to 1/2) and dried under reduced pressure to give 33.6 g (yield: 96%) of the title compound (8).

Workup

customthe resulting reaction mixture
customsolids which precipitated out
customwere separated by filtration
washThe resulting solids were washed with a mixed solution of diethyl ether/ethanol (1/1 to 1/2)
customdried under reduced pressure

Sources & evidence

ORD record: ord-8536ddc0bb234c5b897bb36343c0ccdb
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187690B2

Linked notes

Loading…