Methanol → HCID 59818345, compound

An 8.2 g quantity of a mixture of 4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methanol 16b and 4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbaldehyde 56 [obtained, as a mixture, from a Suzuki coupling by methods described in WO2007/005572] was dissolved along with sulfamic acid (3.3 g) in a mixture of THF (50 mL) and water (50 mL) The solution was cooled in an ice bath. A solution of 80% NaClO2 (2.6 g) in water (50 mL) was added dropwise from an addition funnel. When addition was complete, the mixture was stirred at <8° C. for 1.5 hr. The mixture was quenched by addition of water and extracted with EtOAc. The organic phase was concentrated under reduced pressure to a volume of ˜50 mL and extracted with 2N KOH (20 mL×2). The organic phase was reserved. The aqueous solution was acidified to pH 2, and the solid filtered, to yield 300-400 mg of product 57 as a first crop. The reserved organic solution was concentrated under reduced pressure and the resulting crude product purified by chromatography on silica gel to give a total of 1.4-1.5 g of 57.

1. customobtained, as a mixture, from a Suzuki coupling by methods
2. temperaturewas cooled in an ice bath
3. additionWhen addition
4. customThe mixture was quenched by addition of water
5. extractionextracted with EtOAc
6. concentrationThe organic phase was concentrated under reduced pressure to a volume of ˜50 mL
7. extractionextracted with 2N KOH (20 mL×2)
8. filtrationthe solid filtered

ORD record

ord-ebbe6744e3004f92876e950a670d6728

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233938B2