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

HRID 885330Notes

Reaction equation

HRID 885330 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.[CH3:25]O>>[CH3:25][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

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 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, 3.0 mmol) in MeOH (10 mL) was added thionyl chloride (0.43 mL, 6.0 mmol), and the reaction was heated to 65° C. for 2 hours, and then at room temperature overnight. The mixture was quenched with 1N aqueous NaOH and extracted three times with EtOAc, and the combined organic layers were washed with H2O, dried, and concentrated. The residue was purified by silica gel chromatography (20-40% EtOAc in hexanes) to give the desired product (0.7 g); as well as the acetal by-product.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was quenched with 1N aqueous NaOH
  4. extractionextracted three times with EtOAc
  5. washthe combined organic layers were washed with H2O
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (20-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2bbda38a163c4026be11d52578fcfad8
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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