Triethylamine → HCID 59569687, compound

HRID 2071120Notes

Reaction equation

HRID 2071120 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([O:6][C:7]1[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:9]([CH:8]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 59569687HCID 59569687, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.16 mL, 0.234 g, 2.06 mmol, 1.1 eq) was added to a stirred solution of dimethyl 5-hydroxyisophthalate (0.40 g, 1.86 mmol, 1 eq) and Et3N (0.78 mL, 0.56 g, 5.6 mmol, 3 eq) in 5 mL anhydrous CH2Cl2 at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature over the weekend. The reaction was quenched with water, and the layers were separated. The organic layer was washed with water (×2), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo yielding 0.54 g (1.87 mmol, 100% yield) of dimethyl 5-(methylsulfonyloxy)isophthalate.

Workup

  1. customThe reaction was quenched with water
  2. customthe layers were separated
  3. washThe organic layer was washed with water (×2), brine (×1)
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fe4b292ff8e6491d9d0275ede1def45b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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