Water → Methyl 3'-acetyl-5'-chloro-3-fluoro-2'-methoxy-6'-methylbiphenyl-4-carboxylate

HRID 510879

反応式

HRID 510879 の反応式
Br[C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[C:22]([O:24][CH3:25])=[O:23].O>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([C:4]1[C:3]([O:13][CH3:14])=[C:2]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:16]([F:15])[CH:17]=2)[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)(=[O:12])[CH3:11]

参加物

7

反応物 3

HCID 962WaterHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acidHCID 866667591-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

生成物 1

HCID 86666801Methyl 3'-acetyl-5'-chloro-3-fluoro-2'-methoxy-6'-methylbiphenyl-4-carboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (1.0 g, 3.6 mmol) and [3-fluoro-4-(methoxycarbonyl)phenyl]boronic acid (0.85 g, 4.3 mmol) in 1,4-dioxane (12 mL) and 10% sodium carbonate in water (5.73 mL, 5.40 mmol) was bubbled with N2 to degas. After tetrakis(triphenylphosphine)palladium(0) (166 mg, 0.144 mmol) was added, the mixture was bubbled with N2 for 5 min. more and heated at 100° C. overnight. The mixture was cooled to room temperature and diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with more ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude product.

後処理

  1. customwas bubbled with N2
  2. customto degas
  3. customthe mixture was bubbled with N2 for 5 min. more
  4. temperatureThe mixture was cooled to room temperature
  5. additiondiluted with ethyl acetate
  6. customThe layers were separated
  7. extractionthe aq. layer was extracted with more ethyl acetate
  8. washThe combined extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give crude product

出典と根拠

ORDレコード
ord-b74237beef2345269d14478eb90f3d6b
出典データセット
uspto-grants-2015_08
特許番号
US09096600B2

関連ノート

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