Tetrahydrofuran → HCID 59309639, compound

HRID 1512970Notes

Reaction equation

HRID 1512970 reaction equation
[Cl:1][C:2]1[C:3]([N+:22]([O-])=O)=[CH:4][C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[C:6]([O:8][CH3:9])[CH:7]=1.O1CCCC1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>[Ni](Br)Br.CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[NH2:22]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 593097415-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole

Product 1

HCID 59309639HCID 59309639, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 5-chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole (9.41 g), nickel(II) bromide (0.29 g), tetrahydrofuran (100 mL) and methanol (100 mL) was added sodium borohydride (2.97 g) under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes, and then stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine twice, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/2) to give the title compound (7.77 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringstirred at room temperature for 30 minutes
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/2)

Sources & evidence

ORD record
ord-28cbfbd2958d4096bf3297721378fef3
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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