Water → 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone

HRID 1751529Notes

Reaction equation

HRID 1751529 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)(=O)=O.C([Sn](CCCC)(CCCC)[C:33]([O:35]CC)=[CH2:34])CCC.O.[Br:47]N1C(=O)CCC1=O>CN(C)C=O.ClCCl.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:47][CH2:35][C:33]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:25]=1)=[CH:12][CH:13]=[C:14]1[C:19]=2[O:18][CH2:17][C:16]2[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:15]1=2)=[O:34]

Participants

8

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 867087538-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate

Product 1

HCID 867087542-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanoneYield 70.5%

Reagents, catalysts & solvents 3

HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)CatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8-bromo-6H-dibenzo[c,h]chromen-2-yl trifluoromethanesulfonate (780 mg, 1.7 mmol) and tributyl(1-ethoxyvinyl)stannane (0.86 mL, 2.6 mmol) in dimethylformamide was degassed with a stream of argon for 15 minutes. PdCl2(dppe) (50 mg, 0.086 mmol) was added and the reaction was stirred at room temperature. After 30 hours, water (1 mL) and N-bromosuccinimide (756 mg, 4.2 mmol) were sequentially added to the reaction. After stirring for 2.5 hours at room temperature the reaction was diluted with dichloromethane. The organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine. After the organic layer was dried (Na2SO4) and concentrated, the crude material was recrystallized from dichloromethane and hexanes to yield 2-bromo-1-(8-bromo-6H-dibenzo[c,h]chromen-2-yl)ethanone (518 mg, 57%).

Workup

  1. stirringAfter stirring for 2.5 hours at room temperature the reaction
  2. washThe organics were washed with 5% aqueous LiCl solution, saturated aqueous NaHCO3 solution, and brine
  3. dry with materialAfter the organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe crude material was recrystallized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-6f84fc2e1150415b8872acdfd91b5397
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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