Ethyl bromoacetate → Ethyl [(prop-2-en-1-yl)sulfanyl]acetate

HRID 1074038Notes

Reaction equation

HRID 1074038 reaction equation
[C:1]1([CH2:7][C:8](OCC)=[S:9])C=CC=CC=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(S)C=C>CC[O-].[Na+]>[CH2:8]([S:9][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[CH2:1]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 13367Allyl MercaptanHCID 12284387Ethyl phenylthioacetate

Product 1

HCID 12717294Ethyl [(prop-2-en-1-yl)sulfanyl]acetate

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

The procedure is as in Example 2 for the preparation of ethyl phenylthioacetate, starting with ethyl bromoacetate (16.7 g), a 2M ethanolic solution of sodium ethylate (50 cc) and allylmercaptan (7.7 cc). After purification by chromatography on a silica column with cyclohexane as eluent, ethyl (allylthio)acetate (3.1 g) is obtained, and is used in the crude state in the subsequent phases.

Workup

  1. customAfter purification by chromatography on a silica column with cyclohexane as eluent

Sources & evidence

ORD record
ord-91f249cd31034bc2a566a3015ba0d182
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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