Sodium Bicarbonate → HCID 59377673, compound

HRID 1691789Notes

Reaction equation

HRID 1691789 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9]C)=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59377681HCID 59377681, compound

Product 1

HCID 59377673HCID 59377673, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-4-fluoro-5-methoxy-phenyl)-acetic acid (6.2 g, 23.5 mmol) in dichloromethane (100 ml) was added 1.0 M borontribromide in dichloromathane (94 ml, 94 mml). The mixture was stirred at room temperature for one hour. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromathane. The combined organic extract was washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification by flash chromatography gave (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid (5.2 g, 89%) as a white solid.

Workup

  1. extractionthe mixture was extracted with dichloromathane
  2. extractionThe combined organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-7f52121460694ac1ba0a07c800336bc5
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

Loading…