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

HRID 1817671

反応式

HRID 1817671 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 27826894-(4-Fluorophenyl)benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77c2e4ce4b68472d8f9e6655e4baedc1
出典データセット
uspto-grants-2009_10
特許番号
US07598289B2

関連ノート

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