1,4-Dibromobenzene → HCID 131733144、化合物

HRID 1525295ノート

反応式

HRID 1525295 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li][CH2:10][CH2:11][CH2:12][CH3:13].C1(/C=[N:21]/[S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])CCCCC1.[CH2:28]1[CH2:32]OC[CH2:29]1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:10]([CH2:25][C:24]([CH3:27])([S@@:22]([NH2:21])=[O:23])[CH3:26])[CH:11]2[CH2:32][CH2:28][CH2:29][CH2:13][CH2:12]2)=[CH:3][CH:4]=1

参加物

5

反応物 4

HCID 78041,4-DibromobenzeneHCID 8028Tetrahydrofuran2 回HCID 16655337HCID 16655337、化合物2 回HCID 178418339Butyllithium

生成物 1

HCID 131733144HCID 131733144、化合物収率 22.33%

反応条件

温度
-70 °C

実験手順

1,4-dibromobenzene (20 g, 84.7 mmol) was dissolved in anhydrous THF (300 ml) and the resulting mixture was then cooled to −70° C. Then BuLi (34 mL, 84.6 mmol) was added dropwise at that temperature. The mixture was stirred at −70° C. for 1 hour, then (S,E)-N-(cyclohexylmethylene)-2-methylpropane-2-sulfinamide, 27-a, (14 g, 65 mmol) in anhydrous THF (30 ml) was added dropwise into the mixture at −70° C. The mixture was then stirred overnight from −70° C. to 10° C. The mixture was quenched with saturated NH4Cl followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1) to provide the product, 27-b, (5.4 g, 22.33%). HPLC indicated that the reaction underwent excellent stereoselectivity.

後処理

  1. stirringThe mixture was then stirred overnight from −70° C. to 10° C
  2. customThe mixture was quenched with saturated NH4Cl
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1)

出典と根拠

ORDレコード
ord-40e6d54530ee4527b8485efaecf10aba
出典データセット
uspto-grants-2015_07
特許番号
US09079930B2

反応ノート

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