2,3,5,6-Tetrafluoroaniline → 4-Bromo-2,3,5,6-tetrafluoroaniline
Reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH2:4].[Br:12]Br.C(=O)(O)[O-].[Na+]>CO>[F:1][C:2]1[C:8]([F:9])=[C:7]([Br:12])[C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH2:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3,5,6-Tetrafluoroaniline (25.0 g, 0.15 mol) is dissolved in methanol (100 mL) and treated with elemental bromine (28.4 g, 0.17 mol) by dropwise addition at room temperature. Solid sodium bicarbonate (15 g, 0.18 mol) is added portionwise and the resulting mixture stirred for an additional 2 hours. The reaction mixture is partitioned between Et2O (500 mL) and water (1000 mL). The organic layer is dried (MgSO4) and evaporated by a rotary evaporator to give 2,3,5,6-tetrafluoro-4-bromoaniline (m.p. 59–60° C.).
Workup
- customThe reaction mixture is partitioned between Et2O (500 mL) and water (1000 mL)
- dry with materialThe organic layer is dried (MgSO4)
- customevaporated by a rotary evaporator
Sources & evidence
- ORD record
- ord-906efc43d8134ab7bf0efa1ae004ddbb
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202364B2
Reaction notes
Loading…