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

HRID 1886792Notes

Reaction equation

HRID 1886792 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-845743c54460420f9cd9cd945c796a0d
Source dataset
uspto-grants-2013_08
Patent number
US08501238B2

Reaction notes

Loading…