Chlorosulfonic acid → HCID 86707265, compound

HRID 576046Notes

Reaction equation

HRID 576046 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:14]2)=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH2:14]2)=[CH:9][C:8]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 86707265HCID 86707265, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Chlorosulfonic acid (35.6 mL) was added dropwise to a solution of 1-(7-bromo-3,4-dihydroisoquinolin-2(1 H)-yl)-2,2,2-trifluoroethanone obtained (25.4 g, 82.3 mmol) in chloroform (35 mL) while cooling in ice, and the mixture was stirred at room temperature for 1 hr and at 60° C. for 4 hr. After cooling, the reaction mixture was added dropwise to ice water and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The concentrate was powdered with hexane and ethyl acetate (5:1) and then collected by filtration to afford 7-bromo-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonyl chloride as a pale yellow powder (22.7 g).

Workup

  1. temperaturewhile cooling in ice
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationfollowed by concentration under reduced pressure
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0965c2cd1fc04af3bb6363021b594504
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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