Ethyl bromoacetate → Ethyl 2-[(3,5-dichlorophenyl)thio]acetate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>ClCCl>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][S:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3,5-dichloro-thiophenol (0.50 g, 2.71 mmol) in dichloromethane (8 ml) at 0° C. were added triethylamine (0.49 ml, 3.55 mmol) and a solution of ethyl bromoacetate (0.33 ml, 2.93 mmol) in dichloromethane (2 ml). The resulting solution was stirred at 0° C. for 20 min and then at room temperature for 1 hour. The reaction mixture was then washed sequentially with water and with 1 N aq hydrochloric acid. The organic phase was dried over sodium sulphate, filtered and concentrated in vacuo to yield a light yellow oil (0.72 g, 100%); 1H NMR (300 MHz, CDCl3): 7.26 (2H, d), 7.20 (1H, t), 4.21 (2H, q), 3.65 (2H, s), 1.26 (3H, t).
Workup
- waitat room temperature for 1 hour
- washThe reaction mixture was then washed sequentially with water and with 1 N aq hydrochloric acid
- dry with materialThe organic phase was dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bfae1aa6dad3422194b75343462d407f
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652055B2
Reaction notes
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