Hydrochloric Acid → 2-(4-Bromophenyl)butanoic acid

HRID 735693Notes

Reaction equation

HRID 735693 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH3:15])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[Li+].[OH-].O.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 57082745Ethyl 2-(4-bromophenyl)butanoate

Product 1

HCID 574722-(4-Bromophenyl)butanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 75A (228 mg, 0.85 mmol) in 3 mL THF, was added aq. LiOH (1M, 2 mL, 2 mmol), and the reaction was stirred at rt for 16 h. Water (20 mL) was added, then the mixture was acidified with 1N HCl (pH=2) and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated to afford 75B (150 mg, 73%). MS (ESI) m/z 243.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe organic layer washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a85e526cc7548b6818d7c5303953bb2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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