Oxalyl chloride → 5-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1363129Notes

Reaction equation

HRID 1363129 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:13]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 154910364-(2-Fluorophenyl)butanoic acid

Product 1

HCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-oneYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with 0.15 g of 4-(2-fluorophenyl)butanoic acid, which was dissolved in 20 mL DCM and cooled to 0° C. Oxalyl chloride (0.15 mL) was added, followed by 1 drop of DMF. A drying tube was attached, and the solution was stirred at 0° C. for two hours. Aluminum chloride (0.121 g) was added and the solution was allowed to slowly warm to RT overnight. The mixture was poured onto ice water, and extracted three times with DCM. The combined organic layers were washed with 0.5 M NaOH and brine. The organic phase was dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hexanes), to give 0.07 g (53%) of 5-fluoro-3,4-dihydronaphthalen-1(2H)-one (32).

Workup

  1. customA drying tube was attached
  2. temperatureto slowly warm to RT overnight
  3. additionThe mixture was poured onto ice water
  4. extractionextracted three times with DCM
  5. washThe combined organic layers were washed with 0.5 M NaOH and brine
  6. customThe organic phase was dried
  7. customevaporated
  8. custompurified by column chromatography (eluting with 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8e8aae66838e4480a37be4570f7b8fc9
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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