Hydrochloric Acid → 2-(Benzyloxy)-5-bromobenzoic acid

HRID 1623626Notes

Reaction equation

HRID 1623626 reaction equation
[Li+].[OH-].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([O:11]CC1C=CC=CC=1)=[O:10].Cl>C1COCC1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
71 °C

Procedure

Solid LiOH (5.04 g, 210 mmol) was added to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4, method C, 15 g, 37.8 mmol) in THF (150 ml) and water (50.0 ml) at 20° C. The reaction mixture was stirred at 71° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over Na2SO4 and concentrated to give a white solid. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (3:1) to yield the title compound. 6.1 g.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was isolated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a white solid
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b373d79540794853bce7011d1d89b6c5
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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