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

HRID 509179

반응식

HRID 509179 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-571df04cc54649279b23fb2c5eb47e67
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096565B2

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