Ethyl Acetate → 5-Bromo-4-fluoro-2-(2-fluoro-4-methoxyphenoxy)benzoic acid

HRID 335908ノート

反応式

HRID 335908 の反応式
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[C:12]1[CH:20]=[C:19]([F:21])[C:18]([Br:22])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C(OCC)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Br:22][C:18]1[C:19]([F:21])=[CH:20][C:12]([O:10][C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[F:1])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27745572-Fluoro-4-methoxyphenolHCID 673830652,5-Dibromo-4-fluorobenzoic acid

生成物 1

HCID 673830755-Bromo-4-fluoro-2-(2-fluoro-4-methoxyphenoxy)benzoic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A 2 L RB flask was charged with 2-fluoro-4-methoxyphenol (49.6 g, 349 mmol), 2,5-dibromo-4-fluorobenzoic acid (80 g, 269 mmol), ethyl acetate (1.316 mL, 13.43 mmol), cesium carbonate (192 g, 591 mmol) and toluene (1200 mL). To the mixture at was added copper(I) triflate toluene complex (2:1) (1.713 g, 8.06 mmol) and it was stirred at room temperature for 20 minutes. The solution was then heated to 75° C. for 16 hours at which point the toluene was removed under reduced pressure. The solution was dissolved in 1.5 liters of water and washed with 250 ml of EtOAc. The aqeuous layer was acidified to pH 1 with concentrated HCl and the resulting precipitant was collected by filtration and washed with water. The derived solid was washed with a 1:1 solution of ethyl acetate and hexane, then dried under vacuum to afford 5-bromo-4-fluoro-2-(2-fluoro-4-methoxyphenoxy)benzoic acid as a light brown solid. MS m/z=358.8 [M+H].

後処理

  1. additionTo the mixture at was added copper(I) triflate toluene complex (2:1) (1.713 g, 8.06 mmol) and it
  2. customwas removed under reduced pressure
  3. dissolutionThe solution was dissolved in 1.5 liters of water
  4. washwashed with 250 ml of EtOAc
  5. filtrationthe resulting precipitant was collected by filtration
  6. washwashed with water
  7. washThe derived solid was washed with a 1:1 solution of ethyl acetate and hexane
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-6d12180397b94f46aca8cdd87fa7b645
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

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