Triethylamine → HCID 53908778, compound

HRID 2352670Notes

Reaction equation

HRID 2352670 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[CH:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:3])[CH3:2].[Br:15]Br.C(N(CC)CC)C>CCOCC.O>[C:1]([O:4][CH2:5][CH:6]=[C:7]([Br:15])[S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 54272163HCID 54272163, compound

Product 1

HCID 53908778HCID 53908778, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-hexylthio-2-propenyl acetate (1.3 g, 6.0 mmol) in 10 ml of ether cooled to -10° is added bromine (1.05 g, 0.34 ml, 6.6 mmol). The mixture is stirred at ambient temperature for 30 min., then cooled to 0° and triethylamine (3.0 g, 4.18 ml, 30.0 mmol) is added. The reaction mixture is stirred overnight at RT, then diluted with water and extracted with hexane. The extract is washed with 2N H2SO4, water, saturated NaHCO3 and brine and is dried. The crude product is purified by prep. TLC on silica gel eluting with 20% ethyl acetate/hexane. The upper band is collected to give 3-bromo-3-hexylthio-2-propenyl acetate. The lower band is collected to give 2-bromo-3-hexylthio-2propenyl acetate.

Workup

  1. temperaturecooled to 0°
  2. stirringThe reaction mixture is stirred overnight at RT
  3. extractionextracted with hexane
  4. washThe extract is washed with 2N H2SO4, water, saturated NaHCO3 and brine
  5. customis dried
  6. customThe crude product is purified by prep
  7. customThe upper band is collected

Sources & evidence

ORD record
ord-03ec5f1a241c4787827dd738253b0e9a
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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