(Dimethyl sulfide)trihydroboron → HCID 18782565, compound

HRID 1420830Notes

Reaction equation

HRID 1420830 reaction equation
B.CSC.[Br:5][C:6]1[CH:7]=[C:8]([NH:14][C:15](=O)[C:16]([F:19])([F:18])[F:17])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]>O1CCCC1>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([NH:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[CH:7][C:6]=1[Br:5]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 21584432HCID 21584432, compound

Product 1

HCID 18782565HCID 18782565, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulfide complex (2M in THF, 6.7 ml, 13.4 mmol) was added to a solution of N-(3-Bromo-4-methoxyphenyl)trifluoroacetamide (Description 52, 2.0 g, 6.7 mmol) in tetrahydrofuran (20 ml) and the mixture was heated under reflux for 18 h. The mixture was cooled and the solvent was evaporated under reduced pressure to give the title compound as a yellow oil (2.1 g). 1H NMR (360 MHz, CDCl3) δ6.93 (1H, d, J 2.9 Hz), 6.80 (1H, d, J 8.8 Hz), 6.62 (1H, dd, J 8.8, 2.9 Hz), 3.82 (3H, s), and 3.71 (3H, m). m/z (ES+) 284, 286 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-977514bed8474823aa2ae9aa0273bffc
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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