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

HRID 723263Notes

Reaction equation

HRID 723263 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-41d6cec425a94b24b1cc9bf791cbcb2c
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

Loading…