Hydrochloric Acid → 2-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone

HRID 1871507Notes

Reaction equation

HRID 1871507 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([C:18]1[C:26]([F:27])=[CH:25][C:21]2[S:22][CH:23]=[CH:24][C:20]=2[CH:19]=1)[OH:17].Cl>C(Cl)Cl.C(OCC)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[Cl:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([C:18]1[C:26]([F:27])=[CH:25][C:21]2[S:22][CH:23]=[CH:24][C:20]=2[CH:19]=1)=[O:17]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 154085802-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol

Product 1

HCID 186916002-(2-Chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8.73 ml of oxalyl chloride in 90 ml of methylene chloride is dropwise added 14.2 ml of dimethyl sulfoxide at -70° C. over 30 minutes. The solution is stirred at the same temperature for ten minutes, after which a solution of 11 g of 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol in 90 ml of methylene chloride is dropwise added thereto at the same temperature over 30 minutes. The resulting mixture is stirred at the same temperature for 30 minutes, and then, 50.2 ml of triethylamine is dropwise added thereto. The temperature of the resulting mixture is elevated to room temperature, and thereafter, 200 ml of diethyl ether is added thereto. Then, insolubles are removed from the diethyl ether-added mixture by filtration. Then, the solvent is removed from the resulting filtrate by distillation under reduced pressure. To the residue obtained are added 200 ml of water and 200 ml of ethyl acetate, and then, the pH is adjusted to 1 with 1 N hydrochloric acid. Thereafter, the resulting organic layer is separated, washed successively with water and a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent is removed from the thus dried layer by distillation under reduced pressure. To the residue obtained is added 50 ml of diethyl ether, after which insolubles are collected by filtration, to obtain 9.5 g of colorless, solid 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone.

Workup

  1. customat -70° C.
  2. customover 30 minutes
  3. stirringThe resulting mixture is stirred at the same temperature for 30 minutes
  4. customis elevated to room temperature
  5. customThen, insolubles are removed from the diethyl ether-
  6. additionadded mixture
  7. filtrationby filtration
  8. customThen, the solvent is removed from the resulting filtrate by distillation under reduced pressure
  9. customTo the residue obtained
  10. customThereafter, the resulting organic layer is separated
  11. washwashed successively with water
  12. dry with materiala saturated saline solution and then dried over anhydrous magnesium sulfate
  13. customThe solvent is removed from the thus dried layer by distillation under reduced pressure
  14. customTo the residue obtained
  15. filtrationafter which insolubles are collected by filtration

Sources & evidence

ORD record
ord-1cf7d4c3832347e7abf7ec647ba92418
Source dataset
uspto-grants-2000_08
Patent number
US06103754

Reaction notes

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