N,N-Dimethylaniline → (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate

HRID 2177842Notes

Reaction equation

HRID 2177842 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[C:7]([O:35]C)=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2/[CH:27]=[CH:28]\[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])(=[O:19])=[O:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].CN(C)C1C=CC=CC=1.O>C(Cl)Cl>[Br:5][C:6]1[C:7]([OH:35])=[C:8]([C:13]([CH2:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2/[CH:27]=[CH:28]\[CH2:29][N:30]([CH2:31][CH3:32])[CH2:33][CH3:34])(=[O:18])=[O:19])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 66693679methyl 3-bromo-6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylmethyl]-2-methoxybenzoate2×

Product 1

HCID 66693503(Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminium chloride (0.303 g) was added to a stirred solution of (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-methoxybenzoate (Intermediate 161, 0.528 g) and N,N-dimethylaniline (0.915 g) in DCM (20 ml). The resultant mixture was stirred for 3 hours then a mixture of ice, water and DCM were added. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-6% to give (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate (0.514 g) as a pale purple oil.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  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 a mixture of methanol and DCM with a gradient of 0-6%

Sources & evidence

ORD record
ord-d52889bc82b64cc686deea55b2617b1e
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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