2'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid → Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate

HRID 1662416Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)=[O:15])=[CH:10][C:9]=1[C:17]([O:19][CH3:20])=[O:18]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 66.32B (0.90 g, 3 mmol) in THF (33 mL) at 0° C. was added borane-THF complex (7 mL, 7 mmol, 1.0M). The reaction was allowed to warm to 23° C. and stirred for 7 hours. The reaction mixture was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 66.32C as a colorless solid (0.850 g, 100% yield).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
additionThe reaction was diluted with 1N HCl
extractionextracted three times with EtOAc
dry with materialAfter drying over anhydrous magnesium sulfate
filtrationfiltering
customthe organic solvent was removed under reduced pressure
customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-4ff16315cd374508bee4474bfb6c5402
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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