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

HRID 605839Notes

Reaction equation

HRID 605839 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-7fbe60b1286841ba9bfdeae5bf3d62f7
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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