Chlorotrimethylsilane → Methyl 3-chloro-4,5-dihydroxybenzoate

HRID 62729Notes

Reaction equation

HRID 62729 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].Cl[Si](C)(C)[CH3:15]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:12])[C:10]=1[OH:11])[C:5]([O:7][CH3:15])=[O:6]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 543583-Chloro-4,5-dihydroxybenzoic acid

Product 1

HCID 21649010Methyl 3-chloro-4,5-dihydroxybenzoateYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloro-4,5-dihydroxybenzoic acid (2) (3.16 g, 16.76 mmol) and chlorotrimethylsilane (6.36 mL, 50.3 mmol) in MeOH (50 mL) was stirred at 50° C., under nitrogen overnight. The solvent was removed in vacuo and the residue was partitioned between brine (75 mL) and EtOAc (75 mL). The organic layer was washed with brine (75 mL), dried over MgSO4 and filtered. The solvent was removed in vacuo to give methyl 3-chloro-4,5-dihydroxybenzoate (3) (3.26 g, 13.68 mmol, 82% yield): m/z 201 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 10.17 (2H, br s), 7.38 (1H, d), 7.35 (1H, d), 3.78 (3H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between brine (75 mL) and EtOAc (75 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ab199e7871074ea992abf962aae62c38
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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