Dimethylformamide → 3-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

HRID 1055646ノート

反応式

HRID 1055646 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:17][N:18](C=O)C>[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:17]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:18]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 581374213-Bromo-5-(pentafluorosulfur)benzoic acid

生成物 1

HCID 896998123-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

200 mg (0.61 mmol) of the compound of Example 15A were dissolved in 2.0 ml of DMF, and the mixture was degassed with argon. After addition of 79 mg (0.67 mmol) of zinc cyanide and 42 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium(0), the reaction was stirred in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 120° C. for 30 min. After cooling, solid components were filtered off and the filtrate was separated into its components by preparative HPLC (Method 15). Concentration of the product fractions and drying of the residue under high vacuum gave 115 mg (88% pure, 61% of theory) of the title compound.

後処理

  1. customthe mixture was degassed with argon
  2. temperatureAfter cooling
  3. filtrationsolid components were filtered off
  4. customthe filtrate was separated into its components by preparative HPLC (Method 15)
  5. customConcentration of the product fractions and drying of the residue under high vacuum

出典と根拠

ORDレコード
ord-5c7aab561d204bdfb42ee3f21295f4b7
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

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