p-Toluenesulfonic acid → HCID 18357471, compound

HRID 1422154Notes

Reaction equation

HRID 1422154 reaction equation
[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[O:5][C:6]=1C=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:24]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])OCC>C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[O:5][C:6]=1[CH:24]([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 123372723-Bromo-1-benzofuran-2-carbaldehyde

Product 1

HCID 18357471HCID 18357471, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 2.6 g of 3-bromo-2-benzo[b]furancarboxaldehyde (see M. Cugnon de Sevricourt and M. Robba, Bull. Chim. Soc. Fr., 1977, 142) in 2.7 ml of triethyl orthoformate was added 33 mg of para-toluene sulfonic acid and the solution stirred at at roon temperature overnight. The solution was diluted with a 5% sodium carbonate solution and extracted with ether. The ether extracts were dried over sodium sulfate and evaporated to give 3-bromo-2-(diethoxymethyl)-benzo[b]furan as a liquid; 1H-NMR (200 MHz, CDCl3) d 5.76 (CHOEt).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether extracts were dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-c335a51690a745e5b117030616ee5434
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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