Bromobenzene → 4-(4-Bromophenyl)-2,2-dimethyl-4-oxo-butyric Acid

HRID 9519

반응식

HRID 9519 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1([CH3:16])[CH2:13][C:12](=[O:14])[O:11][C:10]1=[O:15].[Al]>ClC(Cl)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12](=[O:14])[CH2:13][C:9]([CH3:16])([CH3:8])[C:10]([OH:15])=[O:11])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7961BromobenzeneHCID 870672,2-Dimethylsuccinic anhydrideHCID 5359268Aluminum

생성물 1

HCID 219857574-(4-Bromophenyl)-2,2-dimethyl-4-oxo-butyric Acid수율 63%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a chilled solution (ice/water bath) of bromobenzene (7.71 g, 49.1 mmol) and 3,3-dimethyldihydro-2,5-furandione (5.99 g, 46.7 mmol) in dichloroethane (150 mL) was added aluminum trichworide (13.28 g, 99.58 mmol). The ice bath was removed and the reaction mixture was stirred at rt overnight. The mixture was again chilled in an ice/water bath, and then quenched with 1 M aqueous hydrochloric acid. Water (70 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage apparatus, 17:83 ethyl acetate/hexane) to give 4-(4-bromophenyl)-2,2-dimethyl-4-oxobutanoic acid as a white solid (8.34 g, 63%). LC-MS: ret. time 2.79 min; m/z 284.8 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.36 (s, 6H), 3.27 (s, 2H), 7.60 (d, 2H), 7.81 (d, 2H).

후처리

  1. customThe ice bath was removed
  2. temperatureThe mixture was again chilled in an ice/water bath
  3. customquenched with 1 M aqueous hydrochloric acid
  4. additionWater (70 mL) was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (Biotage apparatus, 17:83 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-df37945b51904d399bb64ad4006d4aeb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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