Thionyl Chloride → 13923-56-3

HRID 1836956Notes

Reaction equation

HRID 1836956 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH2:15]O)[CH:3]=1.O=S(Cl)[Cl:19]>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH2:15][Cl:19])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 17604266HCID 17604266, compound

Product 1

HCID 15978213923-56-3Yield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl [4-bromo-2-(hydroxymethyl)phenoxy]acetate (Example 7, 5.00 g, 17.4 mmol) in 150 mL CH2Cl2 under Ar, was added SOCl2 (4.13 g, 34.7 mmol) dropwise with stirring. The mixture was then heated to reflux for 4 hours, cooled, and the volatiles were removed under reduced pressure. The crude oil was then subjected to flash chromatography (15% EtOAc/hexanes) to provide 4.02 g (76%) of the desired product as a clear oil. 1H-NMR (acetone-d6, δ): 1.25 (t, 3H), 3.50 (ddd, 2H), 4.22 (q, 2H), 5.37 (dd, 1H), 6.77 (d, 1H), 7.29 (m, 1H), 7.37 (m, 1H); LRMS (GC/MS/EI) 270 [M]+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-1369995cdf214c789b03d7d87f050819
Source dataset
uspto-grants-2004_08
Patent number
US06780859B2

Reaction notes

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