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Chemical Structure| 5381-20-4 Chemical Structure| 5381-20-4
Chemical Structure| 5381-20-4

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Product Details of Benzo[b]thiophene-3-carbaldehyde

CAS No. :5381-20-4
Formula : C9H6OS
M.W : 162.21
SMILES Code : O=CC1=CSC2=CC=CC=C21
MDL No. :MFCD00052376
InChI Key :WDJLPQCBTBZTRH-UHFFFAOYSA-N
Pubchem ID :227328

Safety of Benzo[b]thiophene-3-carbaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of Benzo[b]thiophene-3-carbaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 5381-20-4 ]
  • Downstream synthetic route of [ 5381-20-4 ]

[ 5381-20-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5381-20-4 ]
  • [ 1196-19-6 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 0℃; for 1 h;
Stage #2: With carbon tetrabromide; triphenylphosphine In dichloromethane for 1 h; Inert atmosphere
To a solution of l-benzothiophene-5-carbaldehyde (800 mg, 5 mmol) in MeOH (10 mL) was added sodium tetrahydroborate (0.28 g, 7.4 mmol) at 0 °C. The reaction mixture was allowed to stir at 0 °C for lh, at which point a saturated aqueous solution of H4C1 (50 mL) and water (50 mL) was added. The mixture was extracted with DCM (3x). The organic solutions were combined, dried over MgS04, filtered, and concentrated to dryness. The crude solid was then dissolved in DCM (100 mL) under argon and triphenyl phosphine (2.30 g, 8.78 mmol) and carbon tetrabromide (2.0 g, 5.9 mmol) were added. After stirring for lh, diethyl ether was added and the resulting mixture was filtered and washed with diethyl ether (2x). The filtrate was concentrated to dryness and the crude residue was purified by column chromatography to afford 5-(bromomethyl)-l-benzothiophene (760 mg, 70 percent) as a white solid. 1H MR (400 MHz, CDCI3) δ 7.80 - 7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.41 (dd, J=8.3, 1.8 Hz, 1H), 7.35 (d, J=5.4 Hz, 1H), 4.68 (s, 2H).
References: [1] Patent: WO2018/89786, 2018, A1, . Location in patent: Paragraph 00376.
 

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