2,3,5,6-Tetrafluoroaniline → 4-Bromo-2,3,5,6-tetrafluoroaniline

HRID 1270710

Reaction equation

HRID 1270710 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

HCID 127862,3,5,6-TetrafluoroanilineHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 6186714-Bromo-2,3,5,6-tetrafluoroaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe reaction mixture is partitioned between Et2O (500 mL) and water (1000 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated by a rotary evaporator

Sources & evidence

ORD record
ord-906efc43d8134ab7bf0efa1ae004ddbb
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Linked notes

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