Dimethylformamide → 5-Chloro-3-methyl-1-benzofuran-2-carbaldehyde

HRID 22751Notes

Reaction equation

HRID 22751 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[C:12]([CH3:15])[C:11]=2[CH:16]=1.CN([CH:20]=[O:21])C>C1COCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH:20]=[O:21])=[C:12]([CH3:15])[C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 114237975-Chloro-3-methylbenzofuranHCID 178418339Butyllithium

Product 1

HCID 47369825-Chloro-3-methyl-1-benzofuran-2-carbaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (2.5 M in hexane, 6.6 mmol, 2.6 mL) was added dropwise over 15 minutes to a solution of 5-chloro-3-methyl benzofuran (6.0 mmol, 1 g) in THF (8 mL) cooled to −78° C. To this was added DMF (12 mmol, 0.6 mL) and stirred for one hour. The reaction mixture was allowed to come to room temperature overnight and then quenched with EtOAc (20 mL) and H2O (10 mL). The organic portion, was collected, dried, filtered and the filtrate was evaporated to dryness to obtain 5-chloro-3-methyl benzofuran-2-carboxaldehyde (96%, 1.12 g), which was carried on without further purification.

Workup

  1. waitto come to room temperature overnight
  2. customquenched with EtOAc (20 mL) and H2O (10 mL)
  3. customThe organic portion, was collected
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7c17e8e25a8046569c9f3b7866a5db29
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

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