Hydrochloric Acid → 2-[3-(3-Bromophenyl)oxetan-3-yl]acetic acid

HRID 1920866Notes

Reaction equation

HRID 1920866 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][C:13]([O:15]CC)=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][C:13]([OH:15])=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57969689Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate

Product 1

HCID 579697372-[3-(3-Bromophenyl)oxetan-3-yl]acetic acidYield 105.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate (1.5 g, 4.513 mmol) was dissolved in MeOH (25 mL) and cooled to 0° C. NaOH (9.026 mL of 1 M, 9.026 mmol) was added and the reaction allowed to warm to rt overnight. The solvent was removed under reduced pressure and the solution neutralised with 2 eq of HCl (1M soln, 9.026 mL) and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure to give 2-[3-(3-bromophenyl)oxetan-3-yl]acetic acid as a viscous yellow oil (1.287 g, 95%).

Workup

  1. temperatureto warm to rt overnight
  2. customThe solvent was removed under reduced pressure
  3. extraction9.026 mL) and extracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-407e38d02ac140549ae9429831a8ba83
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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