m-Bromobenzenethiol → 8-Bromo-2,3,4,5-tetrahydro-5-methyl-1-benzothiepine

HRID 37421

反応式

HRID 37421 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:21]=[CH:20]C2C(=O)CCCS[C:12]=2[CH:11]=1.C[Mg]I>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:11]([CH3:12])[CH2:10][CH2:21][CH2:20][S:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 80597m-BromobenzenethiolHCID 223374568-bromo-3,4-dihydro-2H-benzo[b]thiepin-5-oneHCID 178418373HCID 178418373、化合物

生成物 1

HCID 184061098-Bromo-2,3,4,5-tetrahydro-5-methyl-1-benzothiepine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

First, m-bromothiophenol was converted into 8-bromo-3,4-dihydro-1-benzothiepin-5(2H)-one. This ketone was methylated with MeMgI in ether and the resulting tertiary alcohol was deoxygenated as follows: 22.85 g were placed in 250 ml of hexane under argon and treated in succession with 75.1 g of sodium iodide (NaI), 26.4 ml of acetonitrile and 63.5 ml of Me3SiCl. The mixture was stirred at room temperature overnight, poured on to ice, extracted with ether, washed with bisulfite solution and water, dried and evaporated. Chromatography on silica gel with petroleum ether gave 18.1 g of 8-bromo-2,3,4,5-tetrahydro-5-methyl-1-benzothiepine as a pale yellow oil.

後処理

  1. customthe resulting tertiary alcohol was deoxygenated
  2. additiontreated in succession with 75.1 g of sodium iodide (NaI), 26.4 ml of acetonitrile and 63.5 ml of Me3SiCl
  3. additionpoured on to ice
  4. extractionextracted with ether
  5. washwashed with bisulfite solution and water
  6. customdried
  7. customevaporated

出典と根拠

ORDレコード
ord-8d70d55ea3b44b84bd0ae649b2da03df
出典データセット
uspto-grants-1995_05
特許番号
US05420273

関連ノート

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