Thionyl Chloride → 5-(Chloromethyl)-2,3-dihydro-1h-indene

HRID 1991873Notes

Reaction equation

HRID 1991873 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14]O)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1>C(Cl)(Cl)Cl>[Cl:3][CH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 330183(2,3-dihydro-1H-inden-5-yl)methanol

Product 1

HCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indeneYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (120 ml, 1.65 mol) was added drop-wise to a rapidly stirred mixture of (2,3-dihydro-1H-inden-5-yl)methanol (81.4 g, 0.55 mol) in chloroform (500 ml) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to room temperature and the stirring was continued for an additional 12 h. The chloroform was evaporated under reduced pressure to give a residue, that was purified by column chromatography (petroleum ether:ethyl acetate=15:1) to afford 5-(chloromethyl)-2,3-dihydro-1H-indene (90.5 g, 99%). 1H NMR (300 MHz, CDCl3) δ 2.06-2.19 (m, 4H), 2.93 (t, J=7.5, 4H), 4.54 (s, 2H), 7.15-7.31 (m, 3H).

Workup

  1. additionAfter the addition
  2. customThe chloroform was evaporated under reduced pressure
  3. customto give a residue, that
  4. customwas purified by column chromatography (petroleum ether:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-6a36271ec8dc484b815759f2217b6763
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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