Triethylamine → tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate

HRID 68593

Reaction equation

HRID 68593 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([CH2:17][NH:18][CH3:19])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C.[Cl:27][C:28]1[CH:29]=[C:30]([S:35](Cl)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1[F:34]>C(Cl)Cl>[Br:1][C:2]1[CH:16]=[C:15]([CH2:17][N:18]([CH3:19])[S:35]([C:30]2[CH:31]=[CH:32][C:33]([F:34])=[C:28]([Cl:27])[CH:29]=2)(=[O:37])=[O:36])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 66868764t-Butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate

Product 1

HCID 67527857tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate (2) (68.8 g, 0.21 mol, 1 eq) in DCM (500 mL) was added triethylamine (42 g, 0.42 mol, 2 eq) and 3-chloro-4-fluorobenzene-1-sulfonyl chloride (47.8 g, 0.21 mol. 1 eq, Aldrich, Milwaukee, Wis., USA). After the mixture was stirred for 2 h at room temperature, DCM was evaporate. Crude product was recrystallized from ethanol to yield tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (10) (64 g, 59%).

Workup

  1. customDCM was evaporate
  2. customCrude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-fbe159645fc842e3ada662ef177bc857
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Linked notes

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