Dichloromethane → HCID 14520031, compound

HRID 1607771Notes

Reaction equation

HRID 1607771 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=O.[Na].BrC1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[C:15]2[CH:22]=[O:23].ClCCl>CN1CCCC1=O.O.[Cu]I>[CH3:21][O:20][C:19]1[C:3]([C:2]([F:7])([F:6])[F:1])=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([CH:22]=[O:23])=[C:14]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:13]=[CH:12]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 14520030HCID 14520030, compound

Product 1

HCID 14520031HCID 14520031, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of copper (I) iodide (35.5 g, 0.186 mol), trifluoroacetic acid, sodium salt (50 g, 0.37 mol), and 5-bromo-6-methoxy-2-(phenylmethoxy)-1-naphthalenecarboxaldehyde (17.3 g, 0.047 mol, described in Example 6) in anhydrous 1-methyl-2-pyrrolidinone (150 mL) was stirred vigorously and heated at 180° C. under argon for 1.5 hours, then cooled. The mixture was then suspended in 1 L of water and 1 L of ether and filtered through Solka-Floc*. The filtrate was separated into two phases and the ether layer was washed with water (3X) and then washed with saturated NaCl and dried over Na2SO4. The Solka-Floc filter cake was then washed thoroughly with dichloromethane and the filtrate was washed with water (3X), and then with brine and dried over Na2SO4. After filtration and concentration, the residues from the ether and dichloromethane solutions were combined, dissolved in dichloromethane (250 mL) and filtered through silica gel with additional dichloromethane. The filtrate was concentrated and chromatographed on silica gel with 1:1 hexane:dichloromethane to give 9.8 g (58% yield) of the title compound of suitable purity for subsequent reaction, m.p. 143°-145° C. (from ethanol).

Workup

  1. temperaturecooled
  2. filtration1 L of ether and filtered through Solka-Floc*
  3. customThe filtrate was separated into two phases
  4. washthe ether layer was washed with water (3X)
  5. washwashed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationThe Solka-Floc filter cake
  8. washwas then washed thoroughly with dichloromethane
  9. washthe filtrate was washed with water (3X)
  10. dry with materialwith brine and dried over Na2SO4
  11. filtrationAfter filtration and concentration
  12. dissolutiondissolved in dichloromethane (250 mL)
  13. filtrationfiltered through silica gel with additional dichloromethane
  14. concentrationThe filtrate was concentrated
  15. customchromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-f58f58c92e284f8b9fe7f3d0c861b84a
Source dataset
uspto-grants-1989_09
Patent number
US04866197

Reaction notes

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