p-Fluoronitrobenzene → HCID 11077303, compound

HRID 2415262Notes

Reaction equation

HRID 2415262 reaction equation
[H-].[Na+].[C:3]([NH:10][CH2:11][CH2:12][CH2:13][OH:14])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>O1CCCC1.[Cl-].[NH4+]>[C:6]([O:5][C:3](=[O:4])[NH:10][CH2:11][CH2:12][CH2:13][O:14][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)([CH3:7])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 11077303HCID 11077303, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of sodium hydride (2.48 g, 98.1 mmol) (Aldrich, 95%) in tetrahydrofuran (150 mL) was added a solution of 3-(Boc-amino)-1-propanol (8.1 g, 46.8 mmol) (Aldrich) in tetrahydrofuran (25 mL) at −10° C. After stirred for 15 minutes, the reaction was allowed to warm to room temperature and stirred for a further 30 minute. To this mixture was added a solution of 1-fluoro-4-nitro-benzene (6.92 g, 49.07 mmol) (Aldrich) and the reaction was stirred at room temperature for 2 hours. The resulting mixture was poured in cool aqueous ammonium chloride solution (100 mL). The aqueous layer was extracted with ethyl acetate (3×40 mL) and the combined organic extracts were washed with brine (3×30 mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified on silica gel with 85:15 hexane/ethyl acetate to provide [3-(4-nitrophenoxy)propyl]carbamic acid tert-butyl ester (10.6 g, 73% yield) as light yellow solid. MS (ES) MH+=297.

Workup

  1. stirringstirred for a further 30 minute
  2. stirringthe reaction was stirred at room temperature for 2 hours
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×40 mL)
  4. washthe combined organic extracts were washed with brine (3×30 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified on silica gel with 85:15 hexane/ethyl acetate

Sources & evidence

ORD record
ord-bc3d3db90caf4334be2271fb2492a14c
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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