1,2-Dichloroethane → 2,3-Dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile

HRID 470908

反応式

HRID 470908 の反応式
S(Cl)(Cl)(=O)=O.[F:6][C:7]1[C:15]2C=C[S:12][C:11]=2[C:10]([C:16]#[N:17])=[CH:9][CH:8]=1.[Cl:18][CH2:19][CH2:20][Cl:21]>>[Cl:18][CH:19]1[S:12][C:11]2[C:10]([C:16]#[N:17])=[CH:9][CH:8]=[C:7]([F:6])[C:15]=2[CH:20]1[Cl:21]

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 24648Sulfuryl chlorideHCID 670062384-Fluoro-1-benzothiophene-7-carbonitrile

生成物 1

HCID 685468432,3-Dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile

反応条件

温度
60 °C

実験手順

Sulfuryl chloride (3.0 mL, 37.0 mmol) was added to a solution of 4-fluorobenzo[b]thiophene-7-carbonitrile (1.05 g, 5.93 mmol) in 1,2-dichloroethane (30 mL) at room temperature. The mixture was heated at 60° C. for 24 h and then the solvent was removed and the residue mixed with saturated aq. NaHCO3 solution and extracted with 10% EtOAc in hexanes. These extracts were then washed with saturated aq. NaHCO3 solution, water, brine and dried over Na2SO4. Concentration gave the crude 2,3-dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile as a brown solid (1.57 g). 1H NMR (400 MHz, CDCl3, δ in ppm) 7.68 (dd, J=4.7, 8.6 Hz, 1H), 7.03 (t, J=8.2 Hz, 1H), 5.82 (s, 1H), 5.74 (s, 1H).

後処理

  1. customthe solvent was removed
  2. additionthe residue mixed with saturated aq. NaHCO3 solution
  3. extractionextracted with 10% EtOAc in hexanes
  4. washThese extracts were then washed with saturated aq. NaHCO3 solution, water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration

出典と根拠

ORDレコード
ord-0825316ff768430ebfd8a2db7730b882
出典データセット
uspto-grants-2014_01
特許番号
US08629167B2

関連ノート

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