Sodium Bicarbonate → HCID 58653728, compound

HRID 2220234Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[O:17]C)([CH3:9])[CH3:8])[CH3:2].B(Br)(Br)Br.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:20])([F:21])[F:22])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[OH:17])([CH3:9])[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 3 °C

Procedure

A solution of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid ethyl ester (WO 00/32584) (10.83 g, 30.74 mmol) in dichloromethane (200 ml) is mixed with 1 M boron tribromide-chloroform solution (60 ml) while being cooled in an ice bath, and it is stirred for 3 hours at 2-4° C. The batch is poured onto ice and saturated NaHCO3 solution, and it is stirred for 30 minutes while being cooled with ice. The organic phase is separated, and the aqueous phase is extracted twice more with dichloromethane. The combined, organic extracts are washed with saturated NaCl solution, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue (silica gel) with hexane-ethyl acetate yields 5.36 g of product. Extraction of the aqueous phase with ethyl acetate yields 4.0 g of product again.

Workup

temperaturewhile being cooled in an ice bath
stirringis stirred for 30 minutes
temperaturewhile being cooled with ice
customThe organic phase is separated
extractionthe aqueous phase is extracted twice more with dichloromethane
washorganic extracts are washed with saturated NaCl solution
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-6f79e6de346342ecbfcbe75a6f52ff59
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417056B2

Reaction notes

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