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

HRID 508366

Reaction equation

HRID 508366 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[SH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].CCN(CC)CC.O>CS(C)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]2[CH:6]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:11][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-fluorobenzaldehyde (1.02 g, 4.83 mmol) in DMSO (4 mL), was added ethyl 2-mercaptoacetate (0.58 mL, 5.31 mmol), followed by Et3N (1.35 mL, 9.65 mmol), and the mixture was heated at 80° C. for 3 h. The resulting dark mixture was poured into water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with 10% NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as a light yellow waxy solid (1.29 g, 94%).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic extracts were washed with 10% NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bd1c3a2130d4b158e0c21c2c5a54b5d
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Linked notes

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