Hydrochloric Acid → 2-Bromo-1-(2-chloro-4-methoxyphenyl)-propan-1-one

HRID 1671318

반응식

HRID 1671318 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH:6]([CH3:10])[C:7](Br)=[O:8].[Cl:11][C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1.Cl>ClCCCl>[Br:5][CH:6]([CH3:10])[C:7]([C:17]1[CH:16]=[CH:15][C:14]([O:18][CH3:19])=[CH:13][C:12]=1[Cl:11])=[O:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 178333-ChloroanisoleHCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 110549852-Bromo-1-(2-chloro-4-methoxyphenyl)-propan-1-one

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
0 °C

실험 절차

To a cooled (0° C.) stirring suspension of aluminum chloride (10.89 g, 82 mmol) in DCE (700 ml) is added 2-bromopropionyl bromide (8.66 ml, 82 mmol) followed by 3-chloroanisol (10 ml, 82 mmol) dropwise (rapidly) maintaining the temperature below 5° C. The reaction mixture is stirred at 0° C. for 10 min and RT for 3 hours. The mixture is poured into ice/water (1000 ml) containing 90 ml of 5M HCl. The organic phase is separated and the aqueous portion is washed with DCM (500 ml). The organic extracts are combined, washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 2.5% incraesing to 5% TBME/Hex increasing up to 5% affords the title product. MS: m/z 278.9 [M+H]+

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. stirringThe reaction mixture is stirred at 0° C. for 10 min and RT for 3 hours
  3. customThe organic phase is separated
  4. washthe aqueous portion is washed with DCM (500 ml)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with 2.5%
  9. temperatureincreasing up to 5%

출처 및 근거

ORD 기록
ord-5d65250c9385448499a7f1bb860b543f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994203B2

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