2-Methylbenzenesulfonic acid → 2-Bromo-6-(dimethoxymethyl)pyridine

HRID 2216215Notes

Reaction equation

HRID 2216215 reaction equation
[Br:1][C:2]1[N:7]=[C:6](C=O)[CH:5]=[CH:4][CH:3]=1.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12].C1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:10]([O:13][CH3:14])[O:11][CH3:12])[N:7]=1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 9005Trimethyl orthoformateHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 218860672-Bromo-6-(dimethoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The procedure in Example 6: step b was followed using 6-bromo-pyridine-2-carbaldehyde (600 mg, 3.23 mmol), trimethyl orthoformate (8 mL), and toluenesulfonic acid (100 mg) in MeOH (50 mL). Analogous aqueous workup yielded the product (743 mg) which was used without further purification.

Sources & evidence

ORD record
ord-e32522f29af340119d7d1602fd16c100
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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