Sodium Carbonate → 5'-Bromo-4-(ethylsulfonyl)-2,2'-difluorobiphenyl

HRID 1846030ノート

反応式

HRID 1846030 の反応式
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([F:21])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25](I)[CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([F:29])=[C:27]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[F:21])[CH:28]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 86723254HCID 86723254、化合物

生成物 1

HCID 867232535'-Bromo-4-(ethylsulfonyl)-2,2'-difluorobiphenyl収率 57%

試薬・触媒・溶媒 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-[4-(ethylsulfonyl)-2-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 45, 102 mg, 0.33 mmol) and 4-bromo-1-fluoro-2-iodobenzene (108 mg, 0.36 mmol) in toluene (0.56 mL) and ethanol (0.14 mL) was added aqueous Na2CO3 solution (1M, 0.55 mL, 0.55 mmol). A stream of nitrogen gas was bubbled through the reaction mixture for 5 minutes. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (13 mg, 0.016 mmol) was then added, and the mixture was heated at 80° C. for 1 hour. The reaction mixture was cooled, diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 100:0 to 70:30 to afford the title compound as a light yellow solid in 57% yield, 67 mg.

後処理

  1. customA stream of nitrogen gas was bubbled through the reaction mixture for 5 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with heptane:EtOAc 100:0 to 70:30

出典と根拠

ORDレコード
ord-cacd451e5437456baff41085aa152da3
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

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