Thionyl Chloride → 5-Bromo-1-chloro-2,3-dihydro-1H-indene

HRID 735029Notes

Reaction equation

HRID 735029 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11](O)[CH2:10][CH2:9]2.C(=O)([O-])O.[Na+]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([Cl:3])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 223495155-Bromo-1-chloro-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.09 mL (37.45 mmol) of thionyl chloride, dissolved in cooled dichloromethane, are added dropwise at −10° C. to a solution of 3.8 g (17.83 mmol) of 5-bromoindan-1-ol in 200 mL dichloromethane. The reaction mixture is allowed to come up slowly to ambient temperature and stirred for 14 hours at ambient temperature. Then ice and 100 mL of dilute sodium hydrogen carbonate solution are added successively. The organic phase is extracted twice with 50 mL of water. The combined organic phases are dried over magnesium sulfate, filtered and the solvent is distilled off. Yield: 3.7 g (90% of theory); C9H8BrCl (M=231.52); Rf value: 0.91 (silica gel, petroleum ether/ethyl acetate (6:4)).

Workup

  1. customto come up slowly to ambient temperature
  2. extractionThe organic phase is extracted twice with 50 mL of water
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-c8c49d2cd1ab4a0dbace2e5a9eb1a5cf
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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