Dichloromethane → HCID 59569687, compound

HRID 2243804Notes

Reaction equation

HRID 2243804 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].ClCCl.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:19][S:20]([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 59569687HCID 59569687, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0° C. solution of dimethyl 5-hydroxyisophthalate (2.0 g, 9.5 mmol) in 3:1 dichloromethane:pyridine (100 mL) was added methanesulfonyl chloride (3.6 g, 31.4 mmol). The reaction warmed to room temperature over 18 h. The reaction mixture was concentrated in vacuo. The crude material was diluted with DCM and washed with 1N HCl, H2O (2×), brine, dried with MgSO4, filtered, concentrated and purified by flash chromatography (40 g silica, 25-40% EtOAc/hexanes) to give 1.37 g (50%) of dimethyl 5-[(methylsulfonyl)oxy]isophthalate. 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 8.12 (s, 2H), 3.97 (s, 6H), 3.23 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe crude material was diluted with DCM
  3. washwashed with 1N HCl, H2O (2×), brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (40 g silica, 25-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d26397a79c984c4e9308b541e4ae77f7
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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