Tetra-n-butylammonium tribromide → HCID 86649654, compound

HRID 2367855Notes

Reaction equation

HRID 2367855 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[C:6]([Br:17])[CH:5]=1)(=[O:3])[CH3:2].[Br-:18].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(O)C>[Br:17][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH2:2][Br:18])[CH:9]=[CH:8][C:7]=1[NH:10][C:11](=[O:16])[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 86649655HCID 86649655, compound

Product 1

HCID 86649654HCID 86649654, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-acetyl-2-bromophenyl)-2,2,2-trifluoroacetamide (12.1 g; 39.0 mmol) and tetrabutylammonium tribromide (18.8 g; 39.0 mmol) were dissolved separately in ethanol. After combination, and refluxing for 4 hrs, there was precipitate formation. The solvent was removed. NaHCO3 solution was added to neutralize any residue acid. The solid was filtered, and washed with CH2Cl2, to afford 7.0 g (yield 46%) of product as pale green solid. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H, N—H), 8.51 (d, 3JHH=8.6 Hz, 1H, Ar—H), 8.25 (d, 4JHH=2.0 Hz, 1H, Ar—H), 7.98 (dd, 3JHH=8.6 Hz, 4JHH=2.0 Hz, 1H, Ar—H), 4.38 (s, 2H, —CH2—Br).

Workup

  1. temperatureAfter combination, and refluxing for 4 hrs
  2. customThe solvent was removed
  3. additionNaHCO3 solution was added
  4. filtrationThe solid was filtered
  5. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-73308ee080ab4f0eb4c0c1060951c556
Source dataset
uspto-grants-2014_04
Patent number
US08703096B2

Reaction notes

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