Triacetoxyperiodinane → 5-Bromo-4-methoxy-3-methyl-benzofuran-2-carbaldehyde

HRID 29477Notes

Reaction equation

HRID 29477 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH3:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.CCOCC.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH3:15]

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68711184(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol

Product 1

HCID 860589965-Bromo-4-methoxy-3-methyl-benzofuran-2-carbaldehydeYield 90.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.21 g (0.77 mmole) of 5-bromo-4-methoxy-3-methyl-1-benzofuran-2-yl) methanol (Example 136, Step 1) in 6 mL of dichloromethane, 0.36 g (0.85 mmole, 1.1 eq) of Dess Martin periodinane was added. The reaction was stirred at room temperature for 2 hours and then diluted with 15 mL of ether. To the reaction was added 5 mL of 1NaOH and the mixture was stirred for 30 minutes. The reaction was diluted with ether and water. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to provide 0.19 g of 5-bromo-4-methoxy-3-methyl-1-benzofuran-2-carbaldehyde. Yield 90.4%; m.p. 81-82° C.; MS: 268.9 (M+H)+.

Workup

  1. additionTo the reaction was added 5 mL of 1NaOH
  2. stirringthe mixture was stirred for 30 minutes
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d246cb8b99a942f39e86997e893b1c2e
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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