Ethyl Bromide → Ethyl 4-cyanophenyl sulfide

HRID 2041172ノート

反応式

HRID 2041172 の反応式
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([S:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH3:12]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5850584-Thiobenzonitrile

生成物 1

HCID 21262891Ethyl 4-cyanophenyl sulfide収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Combine 4-mercapto-benzonitrile (0.4 g, 2.96 mmol), bromoethane (1.4 mL, 8.88 mmol) and potassium carbonate (3.3 g, 23.7 mmol) in anhydrous DMF (7 mL) and heat at 60° C. for 17 h. Cool the reaction mixture to ambient temperature and partition between brine (20 mL) and EtOAc (20 mL). Separate the organic layer, dry over anhydrous Na2SO4 and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the desired intermediate as a colorless oil (0.4 g, 83%).

後処理

  1. custompartition between brine (20 mL) and EtOAc (20 mL)
  2. customSeparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

出典と根拠

ORDレコード
ord-cc74c0172f564d5a97ae26690dc8f0fd
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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