Boron tribromide → 2-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuran

HRID 487679Notes

Reaction equation

HRID 487679 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19092726HCID 19092726, compound

Product 1

HCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuranYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 4-tert-butyl-2-(5-methoxybenzofuran-2-yl)thiazole (1.0 g) in dichloromethane (10 ml), 1M solution of boron tribromide in dichloromethane (7 ml) was added dropwise at 5° C. After being stirred for 3 hours, the resulting solution was poured into a mixture of ice and aqueous sodium hydrogen carbonate. The resulting precipitates were collected by filtration and dissolved in a mixture of tetrahydrofuran and water. The solution was concentrated to give crystals of 4-tert-butyl-2-(5-hydroxybenzofuran-2-yl)thiazole (0.91 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutiondissolved in a mixture of tetrahydrofuran and water
  4. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-046100f290044a53b67c82b0d0b67fd1
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

Loading…