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

HRID 731176Notes

Reaction equation

HRID 731176 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.S(Cl)([Cl:14])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([Cl:14])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 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

A solution of 1.1 (2.0 g) in DCM (10 mL) in an ice-bath, was treated with thionyl chloride (10 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into ice water and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated under vacuum. The resulting material was chromatographed on a silica gel column, eluting with 5-10% EtOAc in hexane, to afford 1.2. 1H NMR (DMSO-d6) δ 7.54 (s, 1H), 7.45 (dd, 1H, J1=1.0 Hz, J2=8.50 Hz), 7.37 (d, 1H, J=8.0 Hz), 3.07 (m, 1H), 5.60 (q, 1H), 2.93 (m, 1H), 2.59 (m, 1H), 2.26 (m, 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe resulting material was chromatographed on a silica gel column
  6. washeluting with 5-10% EtOAc in hexane
  7. customto afford 1.2

Sources & evidence

ORD record
ord-53145a8483774032884beb99b5eca7cf
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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