Bromoacetic Acid → 2-(4-Bromo-2,6-dimethylphenoxy)acetic acid

HRID 735707Notes

Reaction equation

HRID 735707 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.Br[CH2:14][C:15]([OH:17])=[O:16]>C1COCC1>[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:14][C:15]([OH:17])=[O:16])=[C:6]([CH3:12])[CH:5]=1

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 169194-Bromo-2,6-dimethylphenolHCID 24758Sodium hydride

Product 1

HCID 7248362-(4-Bromo-2,6-dimethylphenoxy)acetic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (60%, 437 mg, 10.9 mmol) in THF (10 mL) at rt, was added a solution of 4-bromo-2,6-dimethylphenol (1.00 g, 4.97 mmol) in THF (10 mL), over 5 min. The reddish suspension was stirred at rt for 10 min, then a solution of bromoacetic acid (691 mg, 4.97 mmol) in 5 mL THF was added. The suspension was stirred at rt for 20 h. The volatile solvent was evaporated in vacuo, then the mixture was diluted with 20 mL H2O. The pH was adjusted to 7 with 1N HCl, then the aqueous phase was extracted with Et2O (2×). The aqueous phase was acidified to pH=2 with 1N HCl, then was extracted with EtOAc (2×). The combined organic extract washed with brine, dried (Na2SO4) and concentrated to afford 1.10 g (85%) of 79A as a colorless solid. MS (ESI) m/z 259.0 (M+H)+.

Workup

  1. stirringThe suspension was stirred at rt for 20 h
  2. customThe volatile solvent was evaporated in vacuo
  3. additionthe mixture was diluted with 20 mL H2O
  4. extractionthe aqueous phase was extracted with Et2O (2×)
  5. extractionwas extracted with EtOAc (2×)
  6. extractionThe combined organic extract
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa59cd0fd854e8d82c47306ebe97245
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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