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

HRID 1930268Notes

Reaction equation

HRID 1930268 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-f0045c268d1c40818f14487c18a7da1f
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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