Pyrrolidine → 3-Bromo-4-fluoro-5-(pyrrolidine-1-sulfonyl)-benzoic acid

HRID 909393Notes

Reaction equation

HRID 909393 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12](Cl)(=[O:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].CC[N:18]([CH:22]([CH3:24])C)[CH:19]([CH3:21])C.N1CCCC1>O1CCOCC1.O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([N:18]2[CH2:19][CH2:21][CH2:24][CH2:22]2)(=[O:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 509984803-Bromo-4-fluoro-5-(chlorosulfonyl)benzoic acid

Product 1

HCID 674126533-Bromo-4-fluoro-5-(pyrrolidine-1-sulfonyl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 3-Bromo-5-chlorosulfonyl-4-fluoro-benzoic acid (3.0 g) in dioxane/water (9/1 (v/v), 30 ml) was added DiPEA (5 ml) and pyrrolidine (1.55 ml). After stirring for 2 h, the mixture was diluted with EtOAc and washed with 2 M aq. HCl. The organic layer was dried (Na2SO4) and concentrated in vacuo. Yield: 2.3 g.

Workup

  1. washwashed with 2 M aq. HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1739cdca679a4eb99b5f68c8de8e08d0
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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