Pyridine → 2-Pivaloyloxy-5-bromo-6-methylbenzoic acid

HRID 365960

Reaction equation

HRID 365960 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].O1CCCC1.N1C=CC=CC=1>O.C(OCC)(=O)C>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 62493Pivaloyl chlorideHCID 110534513-Bromo-6-hydroxy-2-methylbenzoic acid

Product 1

HCID 232932342-Pivaloyloxy-5-bromo-6-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1B (6.45 g, 28 mmol), pivaloylchloride (3.62 g, 30 mmol), tetrahydrofuran (60 ml) and pyridine (2.45 ml) is stirred at room temperature for 16 hours. The reaction mixture is diluted with water and ethyl acetate. The organic phase is washed with water twice. The organic phase is concentrated in vacuo and the residue is re-crystallized from petrol ethers/diisopropylether (9:1 v/v) yielding the pure product as a white crystals, 6.3 g, (71.6%), mp. 144-145° C.

Workup

  1. washThe organic phase is washed with water twice
  2. concentrationThe organic phase is concentrated in vacuo
  3. customthe residue is re-crystallized from petrol ethers/diisopropylether (9:1 v/v)

Sources & evidence

ORD record
ord-32e49ff7cf8e465b838d4cd342ec1d7d
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Linked notes

Loading…