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

HRID 2374465Notes

Reaction equation

HRID 2374465 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-dbd54c19d9e240e588f73592fd8efa8c
Source dataset
uspto-grants-2008_12
Patent number
US07462633B2

Reaction notes

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