Water → HCID 58968672, compound

HRID 2075038Notes

Reaction equation

HRID 2075038 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:9])=[C:6]([CH3:8])[CH:7]=1.O[CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].S(=O)(=O)(O)O.O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([I:9])=[CH:4][C:3]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]2[C:14](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]1=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8354N-(hydroxymethyl)phthalimideHCID 27246015-Bromo-2-iodotoluene

Product 1

HCID 58968672HCID 58968672, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-bromo-2-iodo toluene (512 mg, 1.72 mmol) in trifluoroacetic acid (5 mL) was added N-(hydroxymethy) phthalimide (305 mg, 1.72 mmol). The mixture developed a pink color. The solution was stirred at room temperature for 22 hours then concentrated sulfuric acid (1 mL) was added. The homogeneous solution was stirred for 18 hours at room temperature. Water was added and the precipitated solid collected by filtration and dried in a current of air (0.776 gm). This material, which by proton NMR analysis contained approximately 15% of an isomeric product, was carried forward to the following procedure without further purification. 1H NMR (400 MHz, CDCl3) δ7.85 (m, 2H) 7.76(m, 2H) 7.5 (s, 1H) 7.38(s, 1H) 4.84(s, 2H) 2.31(s, 3H).

Workup

  1. stirringThe homogeneous solution was stirred for 18 hours at room temperature
  2. filtrationthe precipitated solid collected by filtration
  3. customdried in a current of air (0.776 gm)
  4. customwas carried forward to the following procedure without further purification

Sources & evidence

ORD record
ord-efe8dbc58a7c4612a0cc56d11c8a8e5c
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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