Indane → Indan-5-sulfonyl chloride

HRID 1180657Notes

Reaction equation

HRID 1180657 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:10][S:11](O)(=[O:13])=[O:12]>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:11]([Cl:10])(=[O:13])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10326IndaneHCID 24638Chlorosulfonic acid

Product 1

HCID 3142583Indan-5-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of indane (50 mmol, 6.11 mL) in dichloromethane (50 mL) at 0° C. is added dropwise chlorosulfonic acid (200 mmol, 13.3 mL). The resulting solution is allowed to return to room temperature and stirred for 2 hrs. The solution is then poured slowly onto a mixture of ice (200 g) and dichloromethane (50 mL). The organic layer is separated, washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated to produce indan-5-sulfonic acid chloride.

Workup

  1. customto return to room temperature
  2. customThe organic layer is separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a027879bceaf443895898500b956ff17
Source dataset
uspto-grants-2007_10
Patent number
US07282595B2

Reaction notes

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