1,3-Difluoro-2-(methoxymethoxy)-5-nitrobenzene → HCID 68615412, compound

HRID 730060Notes

Reaction equation

HRID 730060 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[CH:5]=[C:6]([F:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11]>[Pd].CO>[NH2:13][C:4]1[CH:5]=[C:6]([F:12])[C:7]([O:8][CH2:9][O:10][CH3:11])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 1

HCID 686158891,3-Difluoro-2-(methoxymethoxy)-5-nitrobenzene

Product 1

HCID 68615412HCID 68615412, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3,5-difluoro-4-(methoxymethyl)oxynitrobenzene (35.0 g) and palladium catalyst (10% on charcoal, 3.00 g) in methanol (250 mL) ) was hydrogenated at 1 atm for 2 hours at room temperature. After filtration of the catalyst, the filtrate was concentrated in vacuo to give 4-amino-2,6-difluoro-1-(methoxymethyl)oxybenzene. This was used in the next step without further purification. To a solution of crude 4-amino-2,6-difluoro-1-(methoxymethyl)oxybenzene thus obtained in tetrahydrofuran (500 mL) was successively added sodium hydrogencarbonate (17.4 g), water (100 mL) and benzyl chloroformate (30.0 g) at 0° C., and the mixture was stirred at room temperature for 15 minutes. The mixture was diluted with saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=6:1) of the residue gave Reference Example 8 (49.10 g).

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-653a7c81d1be49979263d5f59cc2f810
Source dataset
uspto-grants-2009_09
Patent number
US07582659B2

Reaction notes

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