Iodine → 3-CHLORO-2-IODOPHENYL N,N-DIETHYLCARBAMATE
Reaction equation
C(NC(C)C)(C)C.[Li].[CH2:9]([N:11]([CH2:22][CH3:23])[C:12](=[O:21])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[CH3:10].[I:24]I>O1CCCC1>[CH2:22]([N:11]([CH2:9][CH3:10])[C:12](=[O:21])[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[I:24])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of lithium diisopropylamine (2M in THF) (21.40 ml; 42.8 mmol) in dry tetrahydrofuran (117 ml) under nitrogen atmosphere at −78° C. was added 3-chlorophenyl diethylcarbamate (8.86 g; 38.91 mmol). The reaction mixture was stirred for 30 min at −78° C., and iodine (0.669 g; 46.7 mmol) was added. The solution was stirred for 30 min. at 0° C. and was then allowed to warm up to room temperature for 2 h. The reaction mixture was quenched by adding water and the organics were removed under reduced pressure. The aqueous phase was extracted with ethyl acetate, washed with a solution of hydrochloric acid 1 N, dried over magnesium sulphate, filtered and concentrated under reduced pressure to afford 8.32 g (55%) of 3-chloro-2-iodophenyl diethylcarbamate as brown solid.
Workup
- stirringThe solution was stirred for 30 min. at 0° C.
- temperatureto warm up to room temperature for 2 h
- customThe reaction mixture was quenched
- additionby adding water
- customthe organics were removed under reduced pressure
- extractionThe aqueous phase was extracted with ethyl acetate
- washwashed with a solution of hydrochloric acid 1 N
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3581994a9662447ab829ea1c59a4e38a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785638B2
Reaction notes
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