Ethyl Acetate → 2-Fluoro-6-(2,3,5-trifluorobenzyloxy)-benzonitrile

HRID 2177002

반응식

HRID 2177002 반응식
[H-].[Na+].[F:3][C:4]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:5]=1[CH2:6][OH:7].[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18].CC(=O)OCC>CN(C=O)C>[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([O:7][CH2:6][C:5]2[CH:8]=[C:9]([F:13])[CH:10]=[C:11]([F:12])[C:4]=2[F:3])[C:16]=1[C:17]#[N:18]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 27770302,3,5-Trifluorobenzyl alcohol

생성물 1

HCID 669242262-Fluoro-6-(2,3,5-trifluorobenzyloxy)-benzonitrile수율 72.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a cold (ice water) suspension of sodium hydride (407 mg; 10 mmol) in anhydrous DMF (4 is added a solution of 2,3,5-trifluorobenzyl alcohol (1.62 g; 10 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 1 hour, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1.56 gm; 11 mmol) in anhydrous DMF (5 mL), and allowed to room temperature over 3 hours. TLC (25% EA/Hex) was incomplete so the reaction was continued at room temperature for an additional 2 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting solid is filtered, washed with water, and dried under vacuum at 40° C. for 4.5 hours to give 2.05 grams of 2-fluoro-6-(2,3,5-trifluorobenzyloxy)-benzonitrile.

후처리

  1. waitallowed to room temperature over 3 hours
  2. waitwas continued at room temperature for an additional 2 hours
  3. filtrationthe resulting solid is filtered
  4. washwashed with water
  5. customdried under vacuum at 40° C. for 4.5 hours

출처 및 근거

ORD 기록
ord-d20ea2a180c9470d9b6942ac3c970e66
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067897B2

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