Dimethylformamide → 5-(4-Bromophenoxymethyl)-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole

HRID 1672988ノート

反応式

HRID 1672988 の反応式
Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[CH:4]=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C(#N)C>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:2][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[Cl:14])[N:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[CH:4]=2)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 592400535-bromomethyl-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole

生成物 1

HCID 592402185-(4-Bromophenoxymethyl)-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Into a 25 mL flask was weighed 1.52 g (4.48 mmol) of 5-bromomethyl-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole, 854 mg of 4-bromophenol, 584 mg of sodium carbonate, then 5 mL of DMF, and 5 mL of acetonitrile were added. The resulting suspension was stirred and heated at 80-850C for 20 h then was washed into a separatory funnel with ethyl acetate and water. The ethyl acetate was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Biotage, 80 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo to afford the product as a colorless solid, yield: 1.917 g (99%); 1H NMR (400 MHz, DMSO-d6): δ 7.82 (m, 2H), 7.70 (dt, J=1.5, 7.5 Hz, 1H), 7.62 (dt, J=1.5, 7.5 Hz, 1H), 7.49 (d, J=9 Hz, 2H), 7.27 (s, 1H), 6.92 (d, J=9 Hz, 2H), 5.12 (s, 2H); MS (ES): 431 [M+H]+.

後処理

  1. customInto a 25 mL flask was weighed
  2. temperatureheated at 80-850C for 20 h
  3. washthen was washed into a separatory funnel with ethyl acetate and water
  4. customThe ethyl acetate was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (Biotage, 80 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a60093cdb8de4ccda9438f6410dbda5c
出典データセット
uspto-grants-2011_08
特許番号
US07998995B2

反応ノート

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