Triethylamine → HCID 56648125, compound

HRID 1943292Notes

Reaction equation

HRID 1943292 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([Cl:11])[CH:3]=1.[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].N1CCCC1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]2[CH2:15][CH2:16][CH2:13][CH2:12]2)=[O:8])=[C:4]([Cl:11])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 1088294-Bromo-2-chlorobenzoic acidHCID 111923Propylphosphonic anhydride

Product 1

HCID 56648125HCID 56648125, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-chloro-benzoic acid (30 g, 127.4 mmol) was placed in a 3 L round bottom flask and 1.5 L of EtOAc was transferred into it. Triethylamine (25.8 g, 255 mmol), pyrrolidine (18 g, 255 mmol), and T3P (48.6 g, 152.9 mmol, 50 wt % in EtOAc) were then added. After 1 hr, the reaction was quenched with 200 mL of 1N NaOH and stirred for 10 min. The layers were separated and after 2 more extractions of the aqueous phase with EtOAc (2×500 ml), the combined organic extracts were dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to obtain a viscous oil. Flash chromatography using a 330 g ISCO™ column and 50%, 80% EtOAc/Hexanes yielded the title compound as a light yellow colored viscous oil (35.4 g, 96% yield). Rf=0.25 (50% EtOAc/Hexanes), LRMS m/z Calcd for C11H11BrClNO, 288.6, found, 289.9 (M+H) APCI; 1H-NMR (CDCl3) δ 7.56 (d, J=1.7 Hz, 1H), 7.43 (dd, J=1.7, 8.3 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 3.63 (b apt t, J=6.6 Hz, 2H), 3.17 (B apt t, J=6.6 Hz, 2H), 2.00-1.84 (m, 4H). 13C-NMR (CDCl3) δ 166.0, 136.6, 132.6, 131.3, 130.7, 128.9, 123.3, 48.0, 45.8, 26.1, 24.7.

Workup

  1. customthe reaction was quenched with 200 mL of 1N NaOH
  2. customThe layers were separated
  3. extractionafter 2 more extractions of the aqueous phase with EtOAc (2×500 ml)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto obtain a viscous oil

Sources & evidence

ORD record
ord-72fb7a69de884aa29d65136a5e426b26
Source dataset
uspto-grants-2013_03
Patent number
US08389743B2

Reaction notes

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