Sodium Sulfite → Tert-butyl 3-bromo-5-formylbenzoate

HRID 1257527Notes

Reaction equation

HRID 1257527 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58096191Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate

Product 1

HCID 58095966Tert-butyl 3-bromo-5-formylbenzoateYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-bromo-5-(hydroxymethyl)benzoate (0.8 g, 2.79 mmol) in dichloromethane (14 mL) at 0° C. was added Dess-Martin reagent (1.54 g, 3.62 mmol). The mixture was warmed to ambient temperature. After 1 h, saturated NaHCO3 and saturated Na2SO3 were added the mixture was extracted with dichloromethane (3×) The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→80% hexanes/ethyl acetate) gave the title compound (440 mg).

Workup

  1. extractionwas extracted with dichloromethane (3×) The combined organic extracts
  2. washwere washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→80% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e817a503179643bd8eb1ddf927d6c337
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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