Triacetoxyperiodinane → Methyl 3-bromo-2-methyl-6-(2-oxoethoxy)benzoate

HRID 577570Notes

Reaction equation

HRID 577570 reaction equation
[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([C:9]([O:12][CH2:13][CH:14]=[O:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86723795Methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate

Product 1

HCID 86723796Methyl 3-bromo-2-methyl-6-(2-oxoethoxy)benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate (126a, 126 mg, 0.436 mmol) in DCM (5 mL) was added Dess-Martin periodinane (192 mg, 0.429 mmol). The solution was stirred at room temperature for 2 hours. The solution was purified directly by column chromatography (silica gel, heptanes/EtOAc) to give methyl 3-bromo-2-methyl-6-(2-oxoethoxy)benzoate (126b, 111 mg, 90% yield) as a clear oil.

Workup

  1. customThe solution was purified directly by column chromatography (silica gel, heptanes/EtOAc)

Sources & evidence

ORD record
ord-ce14999c2fdd4e0d803d2443876619b3
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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