4-Nitrophenol → 1-Nitro-4-(prop-2-ynyloxy)benzene

HRID 1770831Notes

Reaction equation

HRID 1770831 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11](Br)[C:12]#[CH:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH2:13]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:12]#[CH:11]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 31171181-Nitro-4-(prop-2-ynyloxy)benzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Nitrophenol (1.00 g, 7.19 mmol), propargyl bromide (80 wt % in toluene; 0.788 mL, 7.09 mmol), and K2CO3 (1.08 g, 7.84 mmol) were stirred in acetone (16.0 mL) at 60° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with water (200 mL). 4-(prop-2-ynyloxy)nitrobenzene was isolated as a white solid by suction filtration (1.12 g). 1H NMR (CDCl3): δ 8.22 (d, J=9.0 Hz, 2H), 7.05 (d, J=9.0 Hz, 2H), 4.80 (d, J=2.4 Hz, 2H), 2.59 (t, J=2.4 Hz, 1H).

Sources & evidence

ORD record
ord-a2c1b4abb43b4e5c9603be9a0d5e0215
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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