Boric Acid → p-Phenylpropiophenone

HRID 1591790노트

반응식

HRID 1591790 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 95230p-Phenylpropiophenone

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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%)

출처 및 근거

ORD 기록
ord-bce2ed3a27c24dc2b58ae2d29b494c26
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291641B2

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