Benzenepropanoic acid → HCID 562815, compound

HRID 1193004Notes

Reaction equation

HRID 1193004 reaction equation
F[B-](F)(F)F.[C:6]1([CH2:12][CH2:13][C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[FH:17].F.F.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[C:6]1([CH2:12][CH2:13][C:14]([F:17])=[O:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 26255TetrafluoroborateHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 562815HCID 562815, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of diethylaminosulfinium tetrafluoroborate (750 mg, 3.3 mmol) in dichloromethane (10 mL) at room temperature was added 3-phenylpropanoic acid (245 mg, 1.6 mmol) and triethylamine trihydrofluoride (266 μl, 1.6 mmol). The reaction mixture was stirred for 24 hours, then an aqueous solution of sodium bicarbonate (5%) was added and stirring was continued for 30 minutes. The organic phase was isolated and dried with magnesium sulphate. The solution was diluted with pentane (10 mL) and the solution was passed through a pad of silica gel with pentane elution. Solvent were evaporated in vacuum to provide 3-phenylpropanoyl fluoride (168 mg, 68%) as a clear liquid. 1H NMR (CDCl3, 300 MHz) δ 7.30-7.17 (m, 5H), 2.96 (t, J=7.6 Hz, 2H), 2.79 (t, J=7.6 Hz, 2H); 19F NMR (CDCl3, 282 MHz) δ 44.8 (s, 1F); 13C NMR (CDCl3, 75 MHz) δ 163.0 (d, 1JC-F=180.2 Hz), 139.1, 128.9, 128.5, 127.0, 34.7 (d, =50.7 Hz), 30.2.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. customThe organic phase was isolated
  4. dry with materialdried with magnesium sulphate
  5. additionThe solution was diluted with pentane (10 mL)
  6. washthe solution was passed through a pad of silica gel with pentane elution
  7. customSolvent were evaporated in vacuum

Sources & evidence

ORD record
ord-01013249a0864cd0a8bb203de503c8a3
Source dataset
uspto-grants-2014_03
Patent number
US08680332B2

Reaction notes

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