4-Fluorobenzyl chloride → HCID 59775159, compound

HRID 1024581Notes

Reaction equation

HRID 1024581 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:13][C:6]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 113483,4-DinitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 59775159HCID 59775159, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3,4-dinitrophenol (1 g, 5.4 mmol) in 30 ml of anhydrous dimethylformamide was treated with 4-fluorobenzyl chloride (0.86 g, 6.0 mmol) and potassium carbonate (1.13 g, 8.2 mmol). The reaction mixture was stirred at room temperature for 24 hours and then poured into 200 ml of ice-water and this mixture was stirred overnight. The solid was filtered and washed with water to give 1.2 g (76%) of tilted compound as a yellow solid after drying in vacuo. 1H NMR (300 MHz, CDCl3) δ: 8.04 (d, J=9.0 Hz, 1H), 7.40 (dd, J=5.4 and 8.7 Hz, 2H), 7.29 (d, J=2.7 Hz, 1H), 7.18 (dd, J=2.7 and 9.0 Hz, 1H), 7.12 (t, J=8.7 Hz, 2H), 5.16 (s, 2H).

Workup

  1. stirringthis mixture was stirred overnight
  2. filtrationThe solid was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-044eed7721cf4f6a8432e086443f555d
Source dataset
uspto-grants-2014_05
Patent number
US08722929B2

Reaction notes

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