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

HRID 605839노트

반응식

HRID 605839 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7fbe60b1286841ba9bfdeae5bf3d62f7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915268B2

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