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

HRID 1671318

反応式

HRID 1671318 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

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]+

後処理

  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%

出典と根拠

ORDレコード
ord-5d65250c9385448499a7f1bb860b543f
出典データセット
uspto-grants-2011_08
特許番号
US07994203B2

関連ノート

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