Chlorosulfonic acid → HCID 86705034, compound

HRID 1053308Notes

Reaction equation

HRID 1053308 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][CH2:12]2>C(Cl)(Cl)Cl>[Br:6][C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 98891Naphthalene, 5-bromo-1,2,3,4-tetrahydro-

Product 1

HCID 86705034HCID 86705034, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

Chlorosulfonic acid (13.80 g, 7.93 ml, 118.00 mmol was added dropwise to a stirred solution of 5-bromo-1,2,3,4-tetrahydronaphthalene (prepared according to the procedure reported in the literature, WO2004/000792, 10.0 g, 47.4 mmol) in 50 ml chloroform at 0° C. The reaction mixture was then allowed to warm to about 25° C. and was stirred at the same temperature for 45 min. The progress of the reaction was monitored by TLC. The reaction mixture was then poured in ice-water (50 ml) and the mixture so obtained was extracted with chloroform (2×150 ml). The combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to obtain the title compound (12.0 g, 81.6%), which was taken ahead as such without further purification for the next step.

Workup

  1. customprepared
  2. customat 0° C
  3. customthe mixture so obtained
  4. extractionwas extracted with chloroform (2×150 ml)
  5. dry with materialThe combined organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00692d43b04d4916afbc41fd59f1c85b
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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