Boron tribromide → (6-Hydroxy-2-oxo-benzooxazol-3-yl)-acetic acid

HRID 1710653Notes

Reaction equation

HRID 1710653 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:9]=2[O:8][C:7]1=[O:17])C.B(Br)(Br)Br>C(Cl)Cl>[OH:15][C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH2:5][C:4]([OH:18])=[O:3])[C:7](=[O:17])[O:8][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57437813(6-Methoxy-2-oxo-benzooxazol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58834368(6-Hydroxy-2-oxo-benzooxazol-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-methoxy-2-oxo-benzooxazol-3-yl)-acetic acid ethyl ester (52) (251 mg, 1 mmol, 1 equiv) in 3 mL of DCM was added BBr3 (0.3 mL, 3 equiv) and the reaction solution was stirred for 1 h. The reaction mixture was quenched by slow addition of water, followed by the addition of EtOAc. The organic layer was isolated and dried over sodium sulfate, filtered, evaporated in vacuo to provide (6-hydroxy-2-oxo-benzooxazol-3-yl)-acetic acid (53).

Workup

  1. customThe reaction mixture was quenched by slow addition of water
  2. additionfollowed by the addition of EtOAc
  3. customThe organic layer was isolated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a304906559f4436798a355843d466044
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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