Sulfuryl chloride → Methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylthio)-phenylacetate

HRID 1975260ノート

反応式

HRID 1975260 の反応式
S(Cl)(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[C:11]([Br:14])[C:12]=1[SH:13].S(Cl)Cl.[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])([CH3:25])[CH3:24].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.CO>[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[C:11]([Br:14])[C:12]=1[S:13][C:30]1[CH:29]=[CH:28][C:27]([O:32][CH3:33])=[C:26]([CH:23]([CH3:25])[CH3:24])[CH:31]=1

参加物

8

反応物 5

HCID 24648Sulfuryl chlorideHCID 25353Sulfur dichlorideHCID 2706232-IsopropylanisoleHCID 6451240Aluminum(III) ChlorideHCID 19101399Methyl 3,5-dibromo-4-mercaptophenylacetate

生成物 1

HCID 19101393Methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylthio)-phenylacetate収率 70%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Sulfuryl chloride (0.9 mL, 0.011 mol) in 5 mL of dichloromethane was added dropwise to a solution of methyl 3,5-dibromo-4-mercaptophenylacetate (3.4 g, 0.11 mol), from Preparation E, in 50 mL dichloromethane. The pale yellow solution was allowed to stand for 1 hour and transferred to an addition funnel. The resulting sulfenyl chloride was then added dropwise to an ice-cooled suspension of 2-isopropylanisole (1.8 g, 0.022 mol) and aluminum chloride (2.8 g, 0.02 mol) in methanol. The reaction mixture was allowed to warm to room temperature and stirred for an additional 15 min. The reaction mixture was then poured on to ice water and extracted twice with dichloromethane. The combined extract was washed with water and brine, dried (Na2SO4), and evaporated on a rotary evaporator. The residue was purified by flash chromatography (silica gel, 5:1 acetone:hexane) to obtain methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylthio)-phenylacetate (3.5 g, 0.007 mol, 70% yield), MP: 73°-76° C.

後処理

  1. customtransferred to an addition funnel
  2. temperaturecooled
  3. extractionextracted twice with dichloromethane
  4. extractionThe combined extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated on a rotary evaporator
  8. customThe residue was purified by flash chromatography (silica gel, 5:1 acetone:hexane)

出典と根拠

ORDレコード
ord-425a00763e3249f08729415c39ea34c6
出典データセット
uspto-grants-1994_02
特許番号
US05284971

反応ノート

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