Triethylamine → Ethyl 6-bromo-1-benzothiophene-2-carboxylate

HRID 2280607Notes

Reaction equation

HRID 2280607 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][SH:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11](F)[CH:10]=1.C(N(CC)CC)C>CS(C)=O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:13]=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[S:3][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl thioglycolate (0.65 g, 5.42 mmol), 4-bromo-2-fluorobenzaldehyde (1.0 g, 4.93 mmol) and triethylamine (1.25 mL, 12.3 mmol) in DMSO (5 mL) was heated at 75° C. for 2 h. The mixture was partitioned between H2O (50 mL) and CH2Cl2 (2×50 mL), and the combined organic layers were dried over Na2SO4. The drying agent was filtered off, and the solvent was removed in vacuo to give the title compound as an oil (1.29 g, 92%).

Workup

  1. customThe mixture was partitioned between H2O (50 mL) and CH2Cl2 (2×50 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationThe drying agent was filtered off
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-263617a9bb174e308712ac2f5fed352b
Source dataset
uspto-grants-2015_09
Patent number
US09139536B2

Reaction notes

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