2-Amino-4-chlorophenol → HCID 16125026, compound

HRID 1373744Notes

Reaction equation

HRID 1373744 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[CH:17]=[CH2:18]>CC(C)=O>[CH2:18]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 72652-Amino-4-chlorophenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 16125026HCID 16125026, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-amino-4-chlorophenol (10 g, 69.65 mmol) and K2CO3 (14.53 g, 105 mmol) in acetone (160 mL) was treated with allyl bromide (9.03 mL, 104 mmol), stirred at room temperature overnight, and filtered. The filter cake was washed with acetone and the combined filtrates were concentrated. The residue was purified by flash column chromatography eluting with hexanes/ethyl acetate (10:1) to provide 8.31 g (65%) of the desired product. MS (DCI/NH3) m/z 184.02 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 4.51 (m, 2H), 5.02 (s, 2H), 5.24 (dd, J=10.53, 1.68 Hz, 1H), 5.42 (m, 1H), 6.04 (m, 1H), 6.47 (dd, J=8.54, 2.44 Hz, 1H), 6.66 (d, J=2.75 Hz, 1H), 6.75 (d, J=8.54 Hz, 1H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with acetone
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was purified by flash column chromatography
  5. washeluting with hexanes/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-5125e6d259004a2884b06ca5daa8e6b3
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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