Boron tribromide → dimethyl 2-hydroxyisophthalate

HRID 2071146Notes

Reaction equation

HRID 2071146 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>C(Cl)Cl>[OH:6][C:7]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15708503Dimethyl 2-methoxybenzene-1,3-dicarboxylate

Product 1

HCID 10889156dimethyl 2-hydroxyisophthalateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (1.0M in CH2Cl2, 7.53 ml, 7.53 mmol, 2.5 eq) was added dropwise to a stirred solution of dimethyl 2-methoxyisophthalate (0.6785 g, 3.01 mmol, 1 eq) in anhydrous CH2Cl2 (4 ml) at 0° C. under Ar. After 30 min the reaction was warmed to room temperature. After 2 h the reaction was quenched anhydrous MeOH (1 ml) and stirred overnight. The solvent was removed in vacuo and the residue dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.4045 g (1.92 mmol, 64% yield) of dimethyl 2-hydroxyisophthalate.

Workup

  1. customAfter 2 h the reaction was quenched anhydrous MeOH (1 ml)
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  5. dry with materialdried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-7cf5219e43044c9caa4730a57144713f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…