Sulfuryl chloride → 3-Chloro-5-(phenylmethoxy)benzenesulfonyl chloride

HRID 1044704ノート

反応式

HRID 1044704 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17](Cl)([Cl:20])(=[O:19])=[O:18]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:17]([Cl:20])(=[O:19])=[O:18])[CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24648Sulfuryl chlorideHCID 532170081-(Benzyloxy)-3-bromo-5-chlorobenzene

生成物 1

HCID 581587373-Chloro-5-(phenylmethoxy)benzenesulfonyl chloride収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under N2 atmosphere, 2.23 g 1-benzyloxy-3-bromo-5-chloro-benzene was dissolved in 50 mL dry THF, and the mixture was cooled in an ice bath. Dropwise, 14.84 mL of a 1M solution of isopropyl magnesium chloride-lithium chloride complex was added, and the mixture was stirred at room temperature overnight. After cooling to −40° C., 2.41 mL of sulfuryl chloride was added in one portion (T raised to 10° C.), and the mixture was stirred for 15 minutes at room temperature. After cooling with an ice bath, the mixture was quenched with water and acidified with 1M aqueous HCl. The mixture was extracted with MTBE, and the organic phase was dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (PA→PA/Et2O 95:5) to yield 1.53 g (62%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.14 (s, 2H), 7.30 (t, J=2 Hz, 1H), 7.34-7.47 (m, 5H), 7.50 (t, J=2 Hz, 1H), 7.62 (t, J=1.5 Hz, 1H).

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. temperatureAfter cooling to −40° C.
  3. stirringthe mixture was stirred for 15 minutes at room temperature
  4. temperatureAfter cooling with an ice bath
  5. customthe mixture was quenched with water
  6. extractionThe mixture was extracted with MTBE
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography (PA→PA/Et2O 95:5)

出典と根拠

ORDレコード
ord-7f7b6cf6ea8a4579b1217a27faa92b57
出典データセット
uspto-grants-2013_10
特許番号
US08563723B2

反応ノート

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