2-Methylbenzenesulfonic acid → 1-Bromo-3-dimethoxymethyl-2-methyl-benzene

HRID 723030Notes

Reaction equation

HRID 723030 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:11]1(C)C(S(O)(=O)=O)=CC=CC=1.[C:22]([O-:25])(O)=O.[Na+]>CO.C(OC)(OC)OC>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]([O:25][CH3:22])[O:6][CH3:11])[C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 516892Sodium BicarbonateHCID 104427433-Bromo-2-methylbenzaldehyde

Product 1

HCID 218860701-Bromo-3-dimethoxymethyl-2-methyl-benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

The 3-bromo-2-methyl-benzaldehyde ((Example 6: step c) 813 mg, 4.08 mmol) was dissolved in dry MeOH (50 mL) and trimethyl orthoformate (8 mL). Toluenesulfonic acid (100 mg) was added and the solution was stirred for 6 h at rt. Solid NaHCO3 (200 mg) was added, the solution was stirred for 30 min, and the volatile components were removed in vacuo. The residue was dissolved in dry EtOAc (10 mL), the solution was filtered (45 micron filter), and the solvent was removed in vacuo. 1H NMR analysis of the crude material (918 mg, 92%) revealed approximately a 90% conversion of the starting material to the title compound, which was used without further purification. 1H-NMR (CDCl3): δ 7.47 (dd, 1H, J=1.2, 8.1 Hz), 7.44 (dd, 1H, J=0.9, 7.9 Hz), 6.99 (t, 1H, J=7.9 Hz), 5.37 (s, 1H), 3.25 (s, 6H), 2.37 (s, 3H).

Workup

  1. stirringthe solution was stirred for 30 min
  2. customthe volatile components were removed in vacuo
  3. dissolutionThe residue was dissolved in dry EtOAc (10 mL)
  4. filtrationthe solution was filtered
  5. filtration(45 micron filter)
  6. customthe solvent was removed in vacuo
  7. customwas used without further purification

Sources & evidence

ORD record
ord-ceaa67f7b5074399b17d4eb0bde38f4a
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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