N,N-Dimethylaniline → Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate

HRID 1778365Notes

Reaction equation

HRID 1778365 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:25]C)[C:18]([Br:27])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C)C1C=CC=CC=1>C(Cl)Cl>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([OH:25])[C:18]([Br:27])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 66685730Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate2×

Product 1

HCID 66685467Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminium chloride (2.16 g) was added to a stirred solution of methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 41, 2.15 g) and N,N-dimethylaniline (3.26 g) in DCM (35 mL) and the resultant mixture was stirred for 50 minutes. Ice water and DCM were added and the organic layer was separated, washed with 1M HCl, dried (Na2SO4), filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with DCM to give methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (1.83 g) as a white solid.

Workup

  1. customthe organic layer was separated
  2. washwashed with 1M HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with DCM

Sources & evidence

ORD record
ord-48df5f01a14941dca0cee0fee93d4de8
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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