1-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanone → 4-(4-Fluorophenyl)benzoic acid

HRID 1817671

반응식

HRID 1817671 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])C)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[O:17](Br)[Na].C(O)(=O)C.C1(C2C=CC=CC=2)C=CC=CC=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:17])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 6081141-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanoneHCID 656671Sodium PyrosulfiteHCID 21957439HCID 21957439, 화합물HCID 178507097sodium hypobromite

생성물 1

HCID 27826894-(4-Fluorophenyl)benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

NaOH (7 g) was dissolved in water (25 mL) and cooled in an ice bath. Bromine (7.8 g) was added dropwise to give a solution of NaOBr. 1-(4′-Fluoro-biphenyl-4-yl)-ethanone (0.01 mol) was dissolved in dioxane (35 mL) and warmed to 50° C. in a water bath. The NaOBr solution was added slowly to the stirred solution of the biphenyl acetate and stirring continued at 50° C. for a further 20 minutes. The solution was allowed to cool and a solution of sodium metabisulphite (8 g in 40 mL water) was added followed by water (170 mL). 50 mL of the liquid was evaporated under reduced pressure with heating. The remainder was acidified with HCl (5 mL) and a white precipitate formed upon cooling. The precipitate was filtered and recrystallised from acetic acid to give the title compound. δC (CDCl3, 62.9 MHz): 115.9, 126.8, 129.2, 129.6, 129.8 (d, J 2.9), 135.5 (d, J 2.9), 143.2, 162.4 (d, J 245.1) and 167.2.

후처리

  1. temperatureto cool
  2. custom50 mL of the liquid was evaporated under reduced pressure
  3. temperaturewith heating
  4. customa white precipitate formed
  5. temperatureupon cooling
  6. filtrationThe precipitate was filtered
  7. customrecrystallised from acetic acid

출처 및 근거

ORD 기록
ord-77c2e4ce4b68472d8f9e6655e4baedc1
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598289B2

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