Fluoroacetyl chloride → HCID 67257868, compound

HRID 1618808Notes

Reaction equation

HRID 1618808 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[O:3][CH2:2]1.[F:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:27](=[O:28])[CH2:26][F:25])[C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 9663Fluoroacetyl chlorideHCID 67258841HCID 67258841, compound

Product 1

HCID 67257868HCID 67257868, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(benzo[1,3]dioxol-4-ylmethyl)-N-(2-phenyloxy-phenyl)amine (0.16 g, 0.50 mmol) dissolved in DCM (2 mL) was added TEA (0.20 g, 2.00 mmol, 0.28 mL). The reaction was cooled to 0° C. and fluoroacetyl chloride (0.10 g, 1.00 mmol, 0.07 mL) was added. The mixture was stirred at room temperature for 1 h. The solvents were removed in vacuo, the residue quenched with water (10 mL), extracted with DCM (2×20 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with DCM (A) and MeOH (B) (1-5% B, 80 g, 4.0 CV, 60 mL/min) to afford 160 mg (84%) of N-(benzo[1,3]dioxol-4-ylmethyl)-2-Fluoro-N-(2-phenyloxy-phenyl)acetamide as a yellow oil. The structure was confirmed by 1H NMR (300 MHz, CDCl3) δ 4.67 (1H, d, J=2 Hz, FCH), 4.83 (1H, d, J=2 Hz, FCH), 4.74 (1H, d, J=14 Hz, ArCH), 5.12 (1H, d, J=14 Hz, ArCH), 5.63 (1H, d, J=1 Hz, OCHO), 5.79 (1H, d, J=1 Hz, OCHO), 6.66-6.88 (6H, m, ArH), 6.96-7.06 (2H, m, ArH), 7.12-7.38 (4H, m, ArH).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue quenched with water (10 mL)
  3. extractionextracted with DCM (2×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvents removed in vacuo
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with DCM (A) and MeOH (B) (1-5% B, 80 g, 4.0 CV, 60 mL/min)

Sources & evidence

ORD record
ord-990bcf0a46f742cface9b56db05d4510
Source dataset
uspto-grants-2014_07
Patent number
US08771641B2

Reaction notes

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