1,2-Dichloroethane → HCID 86624343, compound

HRID 2243806Notes

Reaction equation

HRID 2243806 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:13]=1)[C:8]([OH:10])=[O:9])=[O:4].CN(C1C=CC=CN=1)C.[C:28](O)([CH3:31])([CH3:30])[CH3:29].C(Cl)CCl>C(Cl)Cl>[CH3:18][S:15]([O:14][C:12]1[CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[C:7]([CH:11]=1)[C:8]([O:10][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:9])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6386tert-ButanolHCID 218852-DimethylaminopyridineHCID 86624342HCID 86624342, compound

Product 1

HCID 86624343HCID 86624343, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(methoxycarbonyl)-5-[(methylsulfonyl)oxy]benzoic acid (0.74 g, 2.7 mmol) in DCM (25 mL) was added dimethylaminopyridine (0.165 g, 1.35 mmol) and tert-butanol (0.226 g, 3.05 mmol). The reaction mixture was cooled to 0° C. To the reaction was added EDC (0.569 g, 2.97 mmol). The reaction stirred at 0° C. for 2 h and then warmed to room temp over 16 h. The reaction mixture was washed with 1N HCl, H2O, dried with MgSO4, filtered, concentrated and purified by flash chromatography (25 g silica, 10-30% EtOAc/hexanes) to give 0.74 g (83%) of tert-butyl methyl 5-[(methylsulfonyl)oxy]isophthalate. 1H NMR (400 MHz, CDCl3) δ 8.58 (m, 1H), 8.09 (m, 1H), 8.05 (m, 1H), 3.96 (s, 3H), 3.23 (s, 3H) 1.61 (s, 9H).

Workup

  1. temperaturewarmed to room temp over 16 h
  2. washThe reaction mixture was washed with 1N HCl, H2O
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (25 g silica, 10-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca2b3147f7ed4333a6c357440d1f460c
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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