4-Bromophenacyl bromide → HCID 178441576, compound

HRID 1621260Notes

Reaction equation

HRID 1621260 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=O.[CH3:12][C:13]([C:16]([NH2:18])=[NH:17])([CH3:15])[CH3:14].Cl.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:17]=[C:16]([C:13]([CH3:15])([CH3:14])[CH3:12])[NH:18][CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 178441576HCID 178441576, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2,4′-dibromoacetophenone (4.17 g, 15.0 mmol) in N,N-dimethylformamide (60.0 mL) was treated with t-butylcarbamidine hydrochloride (2.05 g, 15.0 mmol) and K2CO3 (4.15 g, 30.0 mmol) and heated to 50° C. for 4 h. Following cooling, the reaction was quenched with water, diluted with brine, and extracted thrice with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification via flash column chromatography (10-40% EtOAc/hexanes) gave the title compound as a light yellow solid (3.38 g; 81%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.58 (d, J=8.1 Hz, 2H) 7.46 (d, J=8.6 Hz, 2H) 7.18 (s, 1H) 1.42 (s, 9H). MS (ES+) m/e 279/281 [M+H]+.

Workup

  1. temperatureFollowing cooling
  2. customthe reaction was quenched with water
  3. additiondiluted with brine
  4. extractionextracted thrice with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash column chromatography (10-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3ee2924311db40f19a59b92c9172d20a
Source dataset
uspto-grants-2014_07
Patent number
US08772507B2

Reaction notes

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