Potassium Acetate → 4-(5-Benzylbenzo[b]thiophen-2-yl)-3-fluorobenzaldehyde

HRID 2075168Notes

Reaction equation

HRID 2075168 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH2:11]([C:18]1[CH:19]=[CH:20][C:21]2[S:25][CH:24]=[CH:23][C:22]=2[CH:26]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C(=O)C>[CH2:11]([C:18]1[CH:19]=[CH:20][C:21]2[S:25][C:24]([C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=3[F:10])=[CH:23][C:22]=2[CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 109771175-Benzylbenzothiophene

Product 1

HCID 584152824-(5-Benzylbenzo[b]thiophen-2-yl)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-3-fluorobenzaldehyde (40 mg, 0.198 mmol), 5-benzylbenzothiophene (44 mg, 0.198 mmol), potassium acetate (5 mg, 0.05 mmol), tetrakis(triphenylphosphine) palladium(0) (11 mg, 0.010 mmol) and N,N-dimethylacetamide (5 mL) was heated at 150° C. for 12 h. The solvent was evaporated in vacuo and the residue was triturated with water (50 mL) and extracted with dichloromethane (2×100 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes) to give the desired product. 1H NMR (400 MHz, CDCl3) δ 9.90 (s, 1H), 7.64-7.85 (m, 6H), 7.22-7.33 (m, 6H), 4.11 (s, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was triturated with water (50 mL)
  3. extractionextracted with dichloromethane (2×100 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ISCO system, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-763530f67fc047f3b05e72b32e4d6afb
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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