Acetic Acid → 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 2091596ノート

反応式

HRID 2091596 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C(O)(=[O:15])C>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[C:6](=[O:15])[CH2:7][C:8]2([CH3:12])[CH3:11]

参加物

3

反応物 2

HCID 176Acetic Acid2 回HCID 124417856-bromo-1,1-dimethyl-2,3-dihydro-1H-indene

生成物 1

HCID 124417825-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one収率 76%

反応条件

温度
60 °C

実験手順

To a solution of 6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene (3.6 g, 16 mmol) in acetic acid (50 mL) was added to a solution of CrO3 (9.6 g, 96.0 mmol) in 50% aqueous acetic acid (50 mL). This solution was heated for 3 h at 60° C. At completion, the reaction mixture was quenched by the addition of isopropanol (20 mL). The quenched reaction was partitioned between EtOAc (200 mL) and a 0.25 M aqueous NaOH (100 mL). The layers were separated and the organics were extracted with EtOAc (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. After purification by flash chromatography over silica gel (50% EtOAc/hexanes eluent), 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one (2.91 g, 76% yield) was isolated as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.65 (s, 1H), 7.47-7.58 (m, 2H), 2.58 (s, 2H), 1.42 (s, 6H); MS (EI) m/z=240.1 [M+1]+.

後処理

  1. customAt completion, the reaction mixture was quenched by the addition of isopropanol (20 mL)
  2. customThe quenched reaction
  3. customwas partitioned between EtOAc (200 mL)
  4. customThe layers were separated
  5. extractionthe organics were extracted with EtOAc (2×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customAfter purification by flash chromatography over silica gel (50% EtOAc/hexanes eluent)

出典と根拠

ORDレコード
ord-20f9a408f1404a768bc6c64165daec43
出典データセット
uspto-grants-2013_05
特許番号
US08440652B2

反応ノート

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