Boron tribromide → 7-Bromo-2-(morpholin-4-yl)-benzooxazol-4-ol

HRID 2186449Notes

Reaction equation

HRID 2186449 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[C:14]2[O:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:11][C:10]=2[C:9]([O:21]C)=[CH:8][CH:7]=1>ClCCl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([OH:21])=[C:10]2[C:14]=1[O:13][C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[N:11]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 224566577-Bromo-4-methoxy-2-(morpholin-4-yl)-benzooxazole

Product 1

HCID 224566467-Bromo-2-(morpholin-4-yl)-benzooxazol-4-olYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (25.6 ml of a 1.0M in dichloromethane) was added slowly to a stirred solution of 7-bromo-4-methoxy-2-(morpholin-4-yl)-benzooxazole (4.0 g) in dry dichloromethane (100 ml) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 90 mins. The mixture was partitioned between sodium hydrogencarbonate solution (50 ml) and dichloromethane (100 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 30-50% ethyl acetate in heptane afforded the title compound as an off-white solid (1.64 g).

Workup

  1. customThe mixture was partitioned between sodium hydrogencarbonate solution (50 ml) and dichloromethane (100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography on silica eluting with 30-50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-398baf3df020478ca80c7f953c69cfc0
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

Loading…