4-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl Chloride → HCID 178525720, compound

HRID 1984919Notes

Reaction equation

HRID 1984919 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[C:15]([O:23][C:24]([F:27])([F:26])[F:25])[CH:14]=1>C1COCC1.[OH-].[Na+]>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH2:2][C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]2)(=[O:21])=[O:20])=[C:15]([O:23][C:24]([F:26])([F:25])[F:27])[CH:14]=1

Participants

5

Reactant 2

HCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 178511262HCID 178511262, compound

Product 1

HCID 178525720HCID 178525720, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of trans-4-aminomethyl-cyclohexanecarboxylic acid (3.14 g, 20 mmol) in THF (20 mL) and 1 M aqueous sodium hydroxide (42 mL) was added a solution of 4-bromo-2-trifluoromethoxy benzenesulfonyl chloride (6.9 g, 20.4 mmol) in THF (20 mL) and the mixture was stirred for 2 hr at ambient temperature. The resulting mixture was concentrated and 1 M aqueous HCl (45 mL) was added. The resulting precipitate was filtered, washed with water and hexanes to give trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid (7.18 g, 78%) as a white powder.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. addition1 M aqueous HCl (45 mL) was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and hexanes

Sources & evidence

ORD record
ord-f4ad3268fb2145579bd1bef21555e356
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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