Methanol → [3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

HRID 1969020Notes

Reaction equation

[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH:19]=[O:20])[CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].[CH3:27]O>>[CH3:27][O:15][C:14](=[O:16])[CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][C:4]=2[CH:19]=[O:20])[CH:8]=1

Participants

Reactant 4

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 24386Thionyl Chloride

HCID 58237510[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid

Product 1

HCID 58237467[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

Conditions

Temperature: 65 °C

Procedure

To [3-(4-bromo-2-formyl-phenoxy)-phenyl]-acetic acid (1 g, 2.98 mmol) in MeOH (10 mL) was added thionyl chloride (0.43 mL, 5.97 mmol), and the reaction was heated to 65° C. for 2 hours, and then stirred overnight at room temperature. The mixture was neutralized with 1N aqueous NaOH and extracted three times with EtOAc. The combined organic layer was washed with H2O, dried, and concentrated, and the residue was purified by silica gel chromatography (20-40% EtOAc in hexanes) to give the title compound, as well as the corresponding acetal.

Workup

extractionextracted three times with EtOAc
washThe combined organic layer was washed with H2O
customdried
concentrationconcentrated
customthe residue was purified by silica gel chromatography (20-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-5f8715fce2b145179edb1b1afead9d63
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426449B2

Reaction notes

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