Sulfuric Acid → 2-(2-Fluorobenzyl)-3-thiophenecarboxaldehyde

HRID 256912Notes

Reaction equation

HRID 256912 reaction equation
S(=O)(=O)(O)O.C[O:7][CH:8](OC)[C:9]1[CH:13]=[CH:12][S:11][C:10]=1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]>ClCCl>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[CH:8]=[O:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 15728745HCID 15728745, compound

Product 1

HCID 157287462-(2-Fluorobenzyl)-3-thiophenecarboxaldehydeYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To silica gel (100 g), 15% aqueous sulfuric acid (15.4 g), and dichloromethane (400 ml) was added 2-(2-fluorobenzyl)-3-thiophenecarboxaldehyde dimethylacetal and dichloromethane (25 ml). The mixture was stirred for 2.5 hrs. The reaction mixture was filtered. The filter cake was washed with ethyl acetate and dichloromethane. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 0.5-10% ethyl acetate/hexanes) to afford 24.0 g (23.5%) of 2-(2-fluorobenzyl)-3-thiophenecarboxaldehyde.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe filter cake was washed with ethyl acetate and dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash column chromatography (silica gel, 0.5-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-74c9cbe69f214dfba5e32cd6dc78da3e
Source dataset
uspto-grants-1993_11
Patent number
US05260319

Reaction notes

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