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

HRID 2177727Notes

Reaction equation

HRID 2177727 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[C:7]([O:27]C)=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].CN(C)C1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[C:7]([OH:27])=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 67107903Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate2×

Product 1

HCID 67107545Methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoateYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (0.7 g) was added to a stirred solution of methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 68, 0.76 g) and N,N-dimethylaniline (1.27 g) in DCM (8 ml) and the resultant mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and hydrochloric acid (1M) and the organic layer was washed with sodium bicarbonate (saturated aqueous solution), dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was collected by filtration to give methyl 3-bromo-6-(3-chlorobenzenesulphonylmethyl)-2-hydroxybenzoate (0.61 g) as a white solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and hydrochloric acid (1M)
  2. washthe organic layer was washed with sodium bicarbonate (saturated aqueous solution)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was triturated with ether
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-1d9cded88b564d32aaa1bfe7c869971c
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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