Dimethylacetamide → Acetamide, N-(4-cyano-2-fluorophenyl)-

HRID 400597

反応式

HRID 400597 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1.C[C:14]([N:16](C)C)=O>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1)#[N:16]

参加物

6

反応物 2

HCID 31374DimethylacetamideHCID 67593N-(4-bromo-2-fluorophenyl)acetamide

生成物 1

HCID 11344323Acetamide, N-(4-cyano-2-fluorophenyl)-収率 86%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

A solution of N-(4-bromo-2-fluorophenyl)acetamide (12.9 g, 55.4 mmol) in 125 mL of anhydrous dimethyl acetamide was heated in the presence of zinc cyanide (5.53 g, 47.1 mmol) and tetrakis(triphenylphosphine)palladium (0) (5.2 g, 4.5 mmol) at 100° C. for 3 hours. The mixture was diluted with 300 mL of cold water, the resulting solid was filtered, washed with water, and dried. The filtrate was extracted with three 100 mL portions of ethyl acetate and the combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was combined with the solid from the filtration. This combined material was filtered through a silica gel column (100% dichloromethane followed by 100% ethyl acetate) to give 8.5 g of N-(4-cyano-2-fluorophenyl)acetamide as a light cream solid (86% yield).

後処理

  1. filtrationthe resulting solid was filtered
  2. washwashed with water
  3. customdried
  4. extractionThe filtrate was extracted with three 100 mL portions of ethyl acetate
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationThe resulting residue was combined with the solid from the filtration
  9. filtrationThis combined material was filtered through a silica gel column (100% dichloromethane followed by 100% ethyl acetate)

出典と根拠

ORDレコード
ord-14d7c05b20334194b88414297225deb0
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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