Water → Ethyl 5-chloro-3-methyl-1-benzothiophene-2-carboxylate

HRID 1720955Notes

Reaction equation

HRID 1720955 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:16]=[CH:15][C:10]2[S:11][CH:12]=[C:13]([CH3:14])[C:9]=2[CH:8]=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].O>CCCCCC.C(OCC)C>[Cl:6][C:7]1[CH:16]=[CH:15][C:10]2[S:11][C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]([CH3:14])[C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 31731719404-18-3HCID 178418339Butyllithium

Product 1

HCID 14836260Ethyl 5-chloro-3-methyl-1-benzothiophene-2-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium in hexane (2.6M, 2.3 ml) was added to a solution of 5-chloro-3-methylbenzo(b)thiophene (1.0 g, 6 mmol) in ethyl ether (20 ml) stirred at 0° C. under argon. The mixture was stirred for 30 minutes and transferred slowly under argon pressure to a stirred solution of ethyl chloroformate (0.63 g, 6 mmol) in ethyl ether (20 ml). The mixture was stirred at 0° C. for 30 minutes and at 25° C. for 1.5 hours. The mixture was treated with water and the organic phase was dried, concentrated and triturated with hexane to give 1.0 g (67%) of ethyl 5-chloro-3-methylbenzo(b)thiophene-2-carboxylate: mp 92.5°-94° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringThe mixture was stirred at 0° C. for 30 minutes and at 25° C. for 1.5 hours
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customtriturated with hexane

Sources & evidence

ORD record
ord-2ef19a15965149f8a058572a6339f22b
Source dataset
uspto-grants-1996_04
Patent number
US05508306

Reaction notes

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