Oxalyl chloride → HCID 66632440, compound

HRID 1824731Notes

Reaction equation

HRID 1824731 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:25]([O:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)[CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.CN(C=O)C.O.C(OCC)(=O)C>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]([O:30][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:32][CH:33]=2)=[O:14])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 684484-Fluoro-1-naphthoic acidHCID 6451240Aluminum(III) ChlorideHCID 21572690HCID 21572690, compound

Product 1

HCID 66632440HCID 66632440, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

A stirred solution of 4-fluoro-1-naphthoic acid (0.5 g, 2.63 mmol) in anhydrous DCM (10 mL) is treated at room temperature with oxalyl chloride (0.52 g, 4.1 mmol) followed by a few drops of anhydrous DMF. Once bubbling subsided, the clear solution is cooled to 4° C. in an ice bath, and aluminium chloride (0.7 g, 5.25 mmol) is added in one portion. After stirring at 4° C. for 20 min, 1-pentyloxy-naphthalene (0.563 g, 2.63 mmol) is added, and the reaction mixture is allowed to warm gradually to ambient temperature overnight. The reaction mixture is distributed between ethyl acetate (50 mL) and water (250 mL) and extracted. The aqueous phase is additionally washed with fresh ethyl acetate (2×50 mL). The combined organic phases are dried (anhydrous MgSO4), filtered and concentrated in vacuo. The residue is purified by chromatography on silica gel using a Biotage apparatus (Dyax Corp.) and cyclohexane:ethyl acetate (9:1) as eluant to give the desired product (0.996 g, 98%).

Workup

  1. customOnce bubbling
  2. temperatureto warm gradually to ambient temperature overnight
  3. extractionextracted
  4. washThe aqueous phase is additionally washed with fresh ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic phases are dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by chromatography on silica gel using a Biotage apparatus (Dyax Corp.) and cyclohexane:ethyl acetate (9:1) as eluant

Sources & evidence

ORD record
ord-1c05776a1b32432d96b58995e1099935
Source dataset
uspto-grants-2006_05
Patent number
US07045533B2

Reaction notes

Loading…