Methyl 2,4-Dihydroxybenzoate → HCID 86650344, compound

HRID 1186691Notes

Reaction equation

HRID 1186691 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(N[S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])C=CC=CC=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:24][C:23]([F:26])([F:25])[S:20]([O:1][C:2]1[CH:11]=[C:10]([O:12][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 16523Methyl 2,4-DihydroxybenzoateHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 81531Diisopropylethylamine

Product 1

HCID 86650344HCID 86650344, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2,4-dihydroxybenzoate 46 (0.5 g, 2.97 mmol), N-phenyltrifluoro-methanesulfonamide (2.125 g, 5.95 mmol) and DIPEA (1.039 mL, 5.95 mmol) in DCM (15 mL) was stirred at room temperature for 2 days then washed with saturated NaHCO3, brine, dried over MgSO4, filtered and solvent evaporated to provide methyl 2,4-bis(trifluoromethylsulfonyloxy)benzoate 47 (1.14 g, 89% yield) after purification by Biotage (0 to 10% EtOAc in Hexane). LRMS (ESI): (calc.) 431.94 (found) 455.0 (MNa)+

Workup

  1. washthen washed with saturated NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-042809ab053a4532bc036e54bca4df09
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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