Dimethylformamide → 8-Bromo-5,6-difluorochroman-4-one

HRID 1363194ノート

反応式

HRID 1363194 の反応式
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][C:13]([OH:15])=O.CN(C=O)C.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]2[C:9]=1[O:10][CH2:11][CH2:12][C:13]2=[O:15]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 669704713-(2-Bromo-4,5-difluorophenoxy)propanoic acid

生成物 1

HCID 669706288-Bromo-5,6-difluorochroman-4-one収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (1.7 mL, 20 mmol) was added to the solution of 2.8 g (10 mmol) of 3-(2-bromo-4,5-difluorophenoxy)-propanoic acid in 40 mL of anhydrous DCM followed by a drop of DMF. After 1.5 hours, a drying tube was attached and the solution was cooled in an ice-water bath. AlCl3 (1.5 g, 11 mmol) was added and the dark red solution was allowed to slowly reach room temperature while being stirred for 16 hours. The mixture was poured into ice and the organic layer was separated. The aqueous layer was extracted with DCM twice. The combined organic layers were washed with 0.5 N NaOH and brine, then dried over Na2SO4 and concentrated. Column chromatography of this residue with hexane and EtOAc provided 1.9 g of the title compound as an off-white solid (73%). 1H NMR (300 MHz, CDCl3): δ 7.6 (t, 1H), 4.65 (t, 2H), 2.85 (t, 2H).

後処理

  1. customa drying tube was attached
  2. temperaturethe solution was cooled in an ice-water bath
  3. customwas allowed to slowly reach room temperature
  4. additionThe mixture was poured into ice
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with DCM twice
  7. washThe combined organic layers were washed with 0.5 N NaOH and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-3ac8877836074d60aed05ca5116ccd23
出典データセット
uspto-grants-2011_02
特許番号
US07884109B2

反応ノート

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