Water → HCID 78994716, compound

HRID 576060Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][CH2:14][CH2:15]Br)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:17][C:18]1[CH:19]=[C:20]([OH:27])[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25].O>CN(C)C=O>[F:17][C:18]1[CH:19]=[C:20]([O:27][CH2:15][CH2:14][CH2:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25]

Participants

Conditions

Temperature: 85 °C

Procedure

Potassium carbonate (20.7 g, 150 mmol) and 3-phenylpropyl bromide (18.2 mL, 120 mmol) were added to a solution of 3-fluoro-4-nitrophenol (15.7 g, 100 mmol) in N,N-dimethylformamide (200 mL) at room temperature and the mixture was stirred at 85° C. for 6 hr. After cooling to room temperature, water was added to the reaction mixture and the mixture was extracted three times with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and brine and dried over anhydrous sodium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was dried under reduced pressure to afford 2-fluoro-1-nitro-4-(3-phenylpropoxy)benzene as a brown oil (33.2 g).

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted three times with ethyl acetate
washThe organic layer was washed with 1 mol/L hydrochloric acid and brine
dry with materialdried over anhydrous sodium sulfate
filtrationthe desiccant was filtered off
concentrationfollowed by concentration under reduced pressure
customThe resulting residue was dried under reduced pressure

Sources & evidence

ORD record: ord-521345c95f0d450fb74537171d1902b1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035059B2

Reaction notes

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