1,4-Dibromobenzene → 4'-Bromo[1,1'-biphenyl]-3-amine

HRID 253013Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:9])[CH:15]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1,4-Dibromobenzene (311 mg, 1.3 mmol) and 201 mg (1.3 mmol) of 3-aminophenylboronic acid were dissolved in 17 ml of N,N-dimethylformamide and 4.2 ml of water. Tetrakistriphenylphosphine palladium (154 mg, 0.13 mmol) and 211 mg (2.0 mmol) of sodium carbonate were added to the solution, and the mixture was stirred at 80° C. for 3 hr. Ethyl acetate (60 ml) and 8.5 ml of water were added to the reaction solution, and the mixture was filtered through Celite. The organic layer as the filtrate was washed five times with 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and was filtered. The solvent was then removed by distillation. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give 182 mg (yield 57%) of the title compound.

Workup

filtrationthe mixture was filtered through Celite
washThe organic layer as the filtrate was washed five times with 30 ml of water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationwas filtered
customThe solvent was then removed by distillation
customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-6edd673a2769430eb84b816708ba0fdf
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871982B2

Reaction notes

Loading…