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

HRID 1742411Notes

Reaction equation

HRID 1742411 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7](O)[CH2:6][CH2:5]2.N1C=CC=CC=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([Cl:20])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 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 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-indan-1-ol (2.0 grams, 9.38 mmol) and pyridine (1.6 mL, 20 mmol)in CH2Cl2 (20 mL) at 0° C. was added thionyl chloride (2.2 grams, 1.30 mL, 18.7 mmol). The reaction mixture was allowed to warm slowly to room temperature. After 1 hour, the reaction mixture was cooled to 0° C., quenched with saturated aqueous NaHCO3 (10 mL) and diluted with CH2Cl2 (100 mL). The organic layer was separated and washed with saturated NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL), dried over magnesium sulfate (MgSO4) and concentrated in vacuo to give a yellow oil. 1H NMR (250 MHz, CDCl3): d 7.4 (s, 1 H), 7.36 (d, 1 H), 7.20 (d, 1 H), 5.35 (dd, 1 H), 3.15 (m), 2.84 (m), 2.55 (m), 1.83 (m).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched with saturated aqueous NaHCO3 (10 mL)
  3. additiondiluted with CH2Cl2 (100 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL)
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-c20d55fb85344d94b3060a532aa9e223
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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