Formic Acid → 2-(4'-Fluorobiphenyl-4-yl)-2-phenylacetic acid

HRID 509179

Reaction equation

HRID 509179 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:22]([OH:24])=[O:23]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]([OH:24])=[O:23])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 57779630(4'-Fluorobiphenyl-4-yl)(phenyl)methanol

Product 1

HCID 577796832-(4'-Fluorobiphenyl-4-yl)-2-phenylacetic acidYield 6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Compound 12 (600 mg, 2.16 mmol) was dissolved in a 25:1 mixture of concentrated sulfuric acid:formic acid (19.76 mL) and left without stirring for 2 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (20-80%) in hexanes to afford compound 13 as an orange oil (40 mg, 6%). 1H NMR (DMSO-d6) δ (ppm): 7.68-7.64 (m, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.40-7.21 (m, 9H), 5.09 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (20-80%) in hexanes

Sources & evidence

ORD record
ord-571df04cc54649279b23fb2c5eb47e67
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Linked notes

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