Sodium Hydroxide → HCID 67308172, compound

HRID 2061622Notes

Reaction equation

HRID 2061622 reaction equation
[Br:1]Br.[F:3][C:4]([F:20])([F:19])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[Br:1][C:16]1[CH:17]=[CH:18][N:14]([S:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:19])[F:20])=[CH:10][CH:9]=2)(=[O:13])=[O:12])[CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 67307858HCID 67307858, compound

Product 1

HCID 67308172HCID 67308172, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Bromine (4.12 mL, 80.1 mmol) was added to a solution of 1-(4-(trifluoromethyl)phenylsulfonyl)-1H-pyrrole (111) (21 g, 76.2 mmol) in acetic acid (254 mL) and the resulting solution was heated to 100° C. for 1 h. The mixture was diluted with CH2Cl2 and poured slowly into ice cold aqueous sodium hydroxide (3 N). The solution was adjusted to pH 7 with aqueous sodium hydroxide (3 N), extracted with CH2Cl2. The organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 4/1, v/v) to give compound 112 (20.4 g, 57.6 mmol, 75%). MS (ESI) 354.0 (M+H).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified on a silica gel column (eluant hexane/EtOAc, 4/1

Sources & evidence

ORD record
ord-8bbe9c37c8ca416692cb04eaa8152e9c
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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