Sodium Bicarbonate → 5-Bromo-2-fluoro-1-benzofuran

HRID 2108710Notes

Reaction equation

HRID 2108710 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1.C(=O)(O)[O-].[Na+].[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(Cl)(Cl)(Cl)Cl.O.ClCCl.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([F:20])=[CH:7][C:6]=2[CH:13]=1

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 7352475-Bromo-2-benzofurancarboxylic acidHCID 2724933Selectfluor

Product 1

HCID 574391135-Bromo-2-fluoro-1-benzofuran

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Bromobenzofuran-2-carboxylic acid (4.68 g) was suspended in carbon tetrachloride (150 ml) and water (50 ml). To this was added sodium bicarbonate (3.36 g), followed by Selectflor (7.1 g) and the reaction mixture was stirred rapidly for 20 hours. The reaction mixture was diluted with dichloromethane and 2N sodium hydroxide solution. The organic phase was separated, washed with brine and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure at room temperature. The residue was applied to a silica cartridge (20 g) and eluted with diethyl ether. This gave 5-bromo-2-fluoro-1-benzofuran (1.4 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was evaporated under reduced pressure at room temperature
  5. washeluted with diethyl ether

Sources & evidence

ORD record
ord-803883fe7a984091a191394c19c064f6
Source dataset
uspto-grants-2009_04
Patent number
US07514437B2

Reaction notes

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