1-Bromo-2-nitrobenzene → 4'-Methanesulphonyl-2-nitrobiphenyl

HRID 1464046Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-methanesulphonyliodobenzene (18 g), 2-bromonitrobenzene (12.7 g) and copper powder (12 g) was heated at 120° C. for 30 hours to yield a residue which was purified by chromatography on a silica column eluted successively with 5:95 mixture, a 10:90 mixture, a 25:75 mixture and then a 40:60 mixture of ethylacetate and hexane to give 4'-methanesulphonyl-2-nitrobiphenyl (m.p. 178° C.). 4'-methanesulphonyl-2-nitrobiphenyl (5 g) was heated at 90°-95° C. for 6 hours with hydrated sodium sulphide (17.3 g) and ethanol (100 ml) to give 2-amino-4'-methanesulphonylbiphenyl (m.p. 164°-165° C.).

Workup

customto yield a residue which
customwas purified by chromatography on a silica column
washeluted successively with 5:95 mixture
additiona 10:90 mixture, a 25:75 mixture and then a 40:60 mixture of ethylacetate and hexane

Sources & evidence

ORD record: ord-6c98594cf00946d4ac5729efcb61da5f
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302720

Reaction notes

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