Ethylene Glycol → 2-Bromo-4-[1,3]dioxin-2-yl-benzoic acid methyl ester

HRID 2261803Notes

Reaction equation

HRID 2261803 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[Br:12].[CH2:14]([OH:17])[CH2:15]O.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:17][CH2:14][CH:15]=[CH:18][O:11]2)=[CH:6][C:5]=1[Br:12]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 57443308Methyl 2-bromo-4-formylbenzoate

Product 1

HCID 675288602-Bromo-4-[1,3]dioxin-2-yl-benzoic acid methyl esterYield 729.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 2-bromo-4-formyl-benzoic acid methyl ester (440 mg, 1.8 mmol), ethylene glycol (1.1 g, 18 mmol) and p-toluene sulfonic acid (30 mg) in THF (10 mL) is stirred at room temperature overnight. The reaction mixture is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as syrup (380 mg, 73%). LC-ES/MS m/e 287.0 (M+1).

Workup

  1. customThe reaction mixture is partitioned between EtOAc (30 mL) and water (30 mL)
  2. washThe organic phase is washed with brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-3080c20b80154a3d87cf8b0a0f670158
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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