Dimethylformamide → 7-Bromo-5-fluoro-3,4-dihydronaphthalen-1(2H)-one

HRID 2089481노트

반응식

HRID 2089481 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([F:14])[CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH2:9][CH2:10][C:11]2=[O:13])=[C:4]([F:14])[CH:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 606766074-(4-Bromo-2-fluorophenyl)butanoic acid

생성물 1

HCID 591994027-Bromo-5-fluoro-3,4-dihydronaphthalen-1(2H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 4-(4-bromo-2-fluoro-phenyl)-butyric acid (0.625 g, 2.154 mmol) and DMF (0.0084 g, 0.108 mmol) in dichloromethane (10 mL) is added oxalyl chloride (0.558 g, 4.309 mmol). The mixture is stirred for 30 min and concentrated in vacuo at room temperature to give a yellow oil, which is re-dissolved in dichloromethane (20 mL) and added dropwise to aluminum chloride (0.402 g, 3.016 mmol) in dichloromethane (20 mL). The mixture is refluxed for 3.5 hours, and then poured into ice-water. The resulting mixture is extracted twice with diethyl ether. The organic phases are combined, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered through a cotton plug, and concentrated. The resulting residue is purified by silica gel flash chromatography (hexanes-ethyl acetate, 19:1 to 9:1) to afford 7-bromo-5-fluoro-3,4-dihydro-2H-naphthalen-1-one; 1H NMR (400 MHz, CDCl3) δ ppm 2.13-2.19 (m, 2 H), 2.67 (t, J=6.6 Hz, 2 H), 2.90 (t, J=6.2 Hz, 2 H), 7.40 (dd, J=8.5, 1.9 Hz, 1 H), 7.98 (s, 1 H).

후처리

  1. concentrationconcentrated in vacuo at room temperature
  2. customto give a yellow oil, which
  3. temperatureThe mixture is refluxed for 3.5 hours
  4. extractionThe resulting mixture is extracted twice with diethyl ether
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a cotton plug
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (hexanes-ethyl acetate, 19:1 to 9:1)

출처 및 근거

ORD 기록
ord-29d6d011e2b4463489dec32bada90f10
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436035B2

반응 노트

불러오는 중…