2,6-Dimethylphenol → HCID 16765466, compound

HRID 1297757Notes

Reaction equation

HRID 1297757 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[C:6]1=[O:15].C[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](C)[C:22]=1[OH:28]>FC(F)(F)S(O)(=O)=O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:25]2[CH:26]=[CH:21][C:22]([OH:28])=[CH:23][CH:24]=2)([C:25]2[CH:24]=[CH:23][C:22]([OH:28])=[CH:21][CH:26]=2)[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 113352,6-DimethylphenolHCID 15810621-(2-chlorobenzyl)-1H-indole-2,3-dione

Product 1

HCID 16765466HCID 16765466, compound

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

Using a method similar to Example 12, 1-(2-chloro-benzyl)-1H-indole-2,3-dione (300 mg, 1.1 mmol) and 2,6-dimethylphenol (831 mg, 8.83 mmol) in trifluoromethanesulfonic acid (5 mL) gives a crude brown oil. Purify by flash chromatography (CH2Cl2, 10% EtOAc/CH2Cl2, 25% EtOAc/CH2Cl2) and recrystallize the resulting oil from diethyl ether/CH2Cl2/hexanes to give after drying under house vacuum 145 mg (30%) of the title compound as an off-white powder. MS (ES): m/z=442 (M+1), 440 (M−1); 1H NMR(DMSO-d6): δ9.46 (s, 2H), 7.52 (dd, J=1.2 Hz, J=7.8 Hz, 1H), 7.36-7.24 (m, 4H), 7.10 (t, J=7.3 Hz, 1H), 7.01-6.91 (m, 6H), 6.71 (d, J=8.7 Hz, 4H), 5.06 (s, 2H).

Workup

  1. customgives a crude brown oil
  2. customPurify by flash chromatography (CH2Cl2, 10% EtOAc/CH2Cl2, 25% EtOAc/CH2Cl2)
  3. customrecrystallize the resulting oil from diethyl ether/CH2Cl2/hexanes
  4. customto give
  5. dry with materialafter drying under house vacuum 145 mg (30%) of the title compound as an off-white powder

Sources & evidence

ORD record
ord-519a606c8e504436b4e6cd4715cf9603
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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