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

HRID 1055646노트

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HRID 1055646 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c7aab561d204bdfb42ee3f21295f4b7
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394309B2

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