Boric Acid → p-Phenylpropiophenone

HRID 2065986ノート

反応式

HRID 2065986 の反応式
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].B(O)(O)O>O.[Pd](Cl)Cl.C(OCC)(=O)C>[C:12]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 7628Boric AcidHCID 10340Sodium CarbonateHCID 66312p-BromopropiophenoneHCID 78412Phenyl dihydrogen orthoborate

生成物 1

HCID 95230p-Phenylpropiophenone

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture containing phenylboric acid (6.1 g; 50 mmol), 4′-bromopropiophenone (10.65 g; 50 mmol), sodium carbonate (5.3 g; 50 mmol) and palladium chloride (500 mg, 2.8 mmol) in 300 ml of water is heated under reflux for 4 hours. Boric acid (1 g; 0.8 mmol) is then added followed by heating for 30 minutes. Once the mixture has been returned to 23° C., 250 ml of ethyl acetate is added followed by filtering on frit then on GFA paper. The filtrate is decanted and the organic phase is washed with a saturated solution of NaCl before being dried over MgSO4 and concentrated using a rotary evaporator. The precipitate is stirred for 30 minutes in 100 ml of isopentane and 5 ml of dichloromethane. After filtration on frit, the solid is rinsed with isopentane. A cream coloured powder is obtained (8.7 g; 83%). Melting point: 98-99° C. MH+=211.1

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureby heating for 30 minutes
  4. customhas been returned to 23° C.
  5. filtrationby filtering on frit
  6. customThe filtrate is decanted
  7. washthe organic phase is washed with a saturated solution of NaCl
  8. dry with materialbefore being dried over MgSO4
  9. concentrationconcentrated
  10. customa rotary evaporator
  11. filtrationAfter filtration on frit
  12. washthe solid is rinsed with isopentane
  13. customis obtained (8.7 g; 83%)

出典と根拠

ORDレコード
ord-76439bfa9cb541079f04e718e3e78dcc
出典データセット
uspto-grants-2012_10
特許番号
US08288560B2

反応ノート

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