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

HRID 37421

반응식

HRID 37421 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d70d55ea3b44b84bd0ae649b2da03df
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420273

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