Potassium Carbonate → 3,4-Dichlorobiphenyl

HRID 241491ノート

反応式

HRID 241491 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:10]1([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 290134-Bromo-1,2-dichlorobenzeneHCID 66827Phenylboronic Acid

生成物 1

HCID 181023,4-Dichlorobiphenyl収率 30.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture was prepared of 1-Bromo-3,4-dichlorobenzene (20.0 g, 88.5 mmol), phenylboronic acid (13.5 g, 110.6 mmol), triphenylphosphine (2.32 g, 8.85 mmol), potassium carbonate (30.58 g, 221.25 mmol), 150 mL xylenes, and 150 mL water. The mixture was stirred and nitrogen bubbled into it for 20 minutes. Palladium acetate was added (0.99 g, 4.425 mmol) and the mixture was heated at 120° C. under nitrogen overnight. Cooled to room temperature and diluted with water and dichloromethane. The mixture was filtered through Celite and the Celite was washed with water and dichloromethane. The layers were separated and the aqueous layer extracted with dichloromethane. The organic layers were dried over magnesium sulfate, filtered, and evaporated to yield a brown oil. The crude material was purified by column chromatography eluting with hexanes. The cleanest fractions containing product were collected. Obtained 6 g (30%) of clean product.

後処理

  1. customnitrogen bubbled into it for 20 minutes
  2. additionPalladium acetate was added (0.99 g, 4.425 mmol)
  3. temperatureCooled to room temperature
  4. additiondiluted with water and dichloromethane
  5. filtrationThe mixture was filtered through Celite
  6. washthe Celite was washed with water and dichloromethane
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with dichloromethane
  9. dry with materialThe organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto yield a brown oil
  13. customThe crude material was purified by column chromatography
  14. washeluting with hexanes
  15. additionThe cleanest fractions containing product
  16. customwere collected

出典と根拠

ORDレコード
ord-71e60726b9564c6eafbbcc638fd40fe9
出典データセット
uspto-grants-2014_02
特許番号
US08652652B2

反応ノート

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