Diethyl Ether → HCID 20462391, compound

HRID 326102Notes

Reaction equation

HRID 326102 reaction equation
O[CH2:2][CH2:3][S:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].C(OCC)C.P(Br)(Br)[Br:17]>N1C=CC=CC=1>[Br:17][CH2:2][CH2:3][S:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 220049methyl 3-(2-hydroxyethylsulfanyl)propanoate

Product 1

HCID 20462391HCID 20462391, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.2 g. of this ester are dissolved in 27 ml. anhydrous diethyl ether, 0.8 ml. pyridine is added thereto and then 1.9 ml. phosphorus tribromide is added dropwise, while cooling with ice. The reaction mixture is subsequently stirred for 5 hours at ambient temperature. Ice water is then added thereto, followed by extraction with diethyl ether. The extract is washed with water, dried and evaporated to give 10.1 g. of an oil which is chromatographed with 480 g. of silica gel, using ligroin-diethyl ether (2:1 v/v) as elution agent, 7.1 g. methyl 3-(2-bromoethylthio)-propionate being obtained in the form of an oil.

Workup

  1. temperaturewhile cooling with ice
  2. extractionfollowed by extraction with diethyl ether
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto give 10.1 g
  7. customof an oil which is chromatographed with 480 g
  8. washas elution agent, 7.1 g

Sources & evidence

ORD record
ord-73e010cb6b9f4f37bd2005e6db5c91c9
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

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