Oxalyl chloride → 8-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one

HRID 605839ノート

反応式

HRID 605839 の反応式
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C=O)C.C(Cl)Cl>[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:9]=1[O:10][CH2:11][CH2:12][C:13]2=[O:15]

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 15457213-(2-fluorophenoxy)propanoic AcidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 139538178-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one収率 98%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Oxalyl chloride (8.79 mL) and 1 drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0° C. for 2 hours, then aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, then dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hex) to give of the title compound (8.20 g, 98%).

後処理

  1. stirringthe solution was stirred for 16 hours at room temperature
  2. additionThe mixture was poured onto ice water
  3. extractionextracted three times with DCM
  4. washThe combined organics were washed with 0.5M NaOH and brine
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography (eluting with 20% EtOAc/Hex)

出典と根拠

ORDレコード
ord-7fbe60b1286841ba9bfdeae5bf3d62f7
出典データセット
uspto-grants-2011_03
特許番号
US07915268B2

反応ノート

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