Triethylamine → Methyl 6-fluorobenzo[b]thiophene-2-carboxylate

HRID 1625796Notes

Reaction equation

HRID 1625796 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].C(N(CC)CC)C>CS(C)=O>[F:10][C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:12]([C:11]([O:15][CH3:16])=[O:14])[S:13][C:2]=2[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 57350889Methyl 6-fluorobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-difluorobenzaldehyde (5.0 g) in dimethylsulfoxide (100 ml) were added methyl thioglycolate (3.45 ml) and triethylamine (10 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was poured into ice-cold water. The mixture was extracted with ethyl acetate, washed with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to give 6-fluoro-2-methoxycarbonylbenzo[b]thiophene (1.32 g) as colorless powder. GC-EI-Mass m/Z 210 (M).

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-adeed1c6a7bf440394e2d35ba7da98a9
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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