Hydrochloric Acid → 4-(4-Bromo-3-formyl-phenoxy)-2-methoxy-benzoic acid ethyl ester

HRID 1483652Notes

Reaction equation

HRID 1483652 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([CH:19]3OCC[O:20]3)[CH:13]=2)=[CH:7][C:6]=1[O:24][CH3:25])[CH3:2].Cl>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([CH:19]=[O:20])[CH:13]=2)=[CH:7][C:6]=1[O:24][CH3:25])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579690074-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-methoxy-benzoic acid ethyl ester

Product 1

HCID 579689314-(4-Bromo-3-formyl-phenoxy)-2-methoxy-benzoic acid ethyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 6 (5.6 g, 13.23 mmol) in THF (50 mL) at 0° C. was added 2N HCl (50 mL). The resulting mixture was stirred at rt O/N. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to give crude product, which was purified by column chromatography (silica gel, 10% EtOAc in hexane) to afford the title compound 7 (3.0 g, 60%) as a pale yellow solid.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give crude product, which
  5. customwas purified by column chromatography (silica gel, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-698c6a0e87054016a89d0ddb5017dd30
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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