Thionyl Chloride → HCID 21202943, compound

HRID 1979074Notes

Reaction equation

HRID 1979074 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][C:11](O)=[O:12]>>[Br:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][C:11]([Cl:3])=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 702285(3-bromophenoxy)acetic acid

Product 1

HCID 21202943HCID 21202943, compound

Procedure

Thionyl chloride (5 ml, 70 mmol) is added at ambient temperature to 3-bromophenoxyacetic acid (5.77 g, 25 mmol). The reaction mixture is brought to reflux for 2 hours. After returning to ambient temperature, it evaporates and the acid chloride is used. The 3-bromophenoxyacetyl chloride previously obtained is dissolved in dichloromethane (150 ml) and added to a solution of aluminum chloride (6.7 g, 50 mmol) in 50 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 30 minutes and then poured into a an equal volume water-ice mixture (400 ml). The mixture is extracted with dichloromethane, dried over MgSO4 filtered and evaporated. The raw product is purified by flash chromatography on silica (eluent petroleum ether ether=100:10). 0.96 g of 6-bromo-3-coumarone is obtained (yield=18%) of formula:

Workup

  1. temperatureto reflux for 2 hours
  2. customAfter returning to ambient temperature
  3. customit evaporates

Sources & evidence

ORD record
ord-fcc6d418939c47ddb4dd3b14a8e03b74
Source dataset
uspto-grants-2001_05
Patent number
US06239284B1

Reaction notes

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