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Chemical Structure| 1378390-29-4 Chemical Structure| 1378390-29-4
Chemical Structure| 1378390-29-4

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Product Details of 3-(2-Bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

CAS No. :1378390-29-4
Formula : C19H15BrO3
M.W : 371.22
SMILES Code : O=C1CCCC2=CC(C3=CC=C(C(CBr)=O)C=C3CO4)=C4C=C21
MDL No. :MFCD30187855
InChI Key :NEADWTKOYDYIHL-UHFFFAOYSA-N
Pubchem ID :86688342

Safety of 3-(2-Bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H290
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338-P310-P406-P405
Class:8
UN#:3261
Packing Group:

Application In Synthesis of 3-(2-Bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1378390-29-4 ]

[ 1378390-29-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 364750-81-2 ]
  • [ 1378390-29-4 ]
  • [ 1378390-66-9 ]
YieldReaction ConditionsOperation in experiment
69% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 3h; 2S,4S)-l-teri-butyl 2-(2-oxo-2-(8-oxo-8,9,l 0,11 -tetrahydro-5H-dibenzo [c,g] chromen-3-yl)ethyl) 4-methylpyrrolidine-l,2-dicarboxylate To a solution of 3-(2-bromoacetyl)-10,l l-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (647 mg, 1.74 mmol) in MeCN (20 mL) was added ((2S,4S)-l -(tert-butoxycarbonyl)-4-methylpyrrolidine- 2-carboxylic acid (559 mg, 2.44 mmol) and DIPEA (0.36 mL, 2.09 mmol) and the solution was heated to 60 °C. After stirring for 3 h, the solution was cooled to rt, and diluted with EtOAc and washed successively with saturated aqueous NaHCC>3 and brine. The organics were dried over MgS04, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (20percent to 50percent EtOAc/hexanes) to afford (2S,4S)-1 -tert-butyl 2-(2-oxo-2-(8- oxo-8,9, 10,11 -tetrahydro-5H-dibenzo [c,g]chromen-3-yl)ethyl) 4-methylpyrrolidine- 1 ,2-dicarboxylate (621 mg, 69percent).
69% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 3h; To a solution of 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (647 mg, 1.74 mmol) in MeCN (20 mL) was added ( <strong>[364750-81-2](2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid</strong> (559 mg, 2.44 mmol) and DIPEA (0.36 mL, 2.09 mmol) and the solution was heated to 60° C. After stirring for 3 h, the solution was cooled to rt, and diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (20percent to 50percent EtOAc/hexanes) to afford (2S,4S)-1-tert-butyl 2-(2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl) 4-methylpyrrolidine-1,2-dicarboxylate (621 mg, 69percent).
  • 2
  • [ 334769-80-1 ]
  • [ 1378390-29-4 ]
  • [ 1378390-26-1 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; In acetonitrile; at 50℃; for 15h; To a solution of 3-(2-bromoacetyl)-10,l l -dihydro-5H-dibenzo[c,g]chromen-8(9H)-one in MeCN (30 mL) was added (2S,5S)-l -(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid (1.2 g, 3.23 mmol) and triethyl amine (0.48 mL, 3.55 mmol) and the solution was heated to 50 °C. After stirring for 15 h, the solution was cooled to rt, and diluted with EtOAc and washed successively with saturated aqueous NaHCC>3 and brine. The organics were dried over MgSO i, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (20percent to 50percent> EtOAc/hexanes) to afford (2S,5S)-1 -tert-butyl 2-(2-oxo-2-(8-oxo- 8,9,10, 11 -tetrahydro-5H-dibenzo[c,g] chromen-3 -yl)ethyl) 5-methylpyrrolidine-l ,2-dicarboxylate (1.09 g, 65percent).
65% With triethylamine; In acetonitrile; at 50℃; for 15h; To a solution of 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one in MeCN (30 mL) was added <strong>[334769-80-1](2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid</strong> (1.2 g, 3.23 mmol) and triethyl amine (0.48 mL, 3.55 mmol) and the solution was heated to 50° C. After stirring for 15 h, the solution was cooled to rt, and diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (20percent to 50percent EtOAc/hexanes) to afford (2S,5S)-1-tert-butyl 2-(2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl) 5-methylpyrrolidine-1,2-dicarboxylate (1.09 g, 65percent).
 

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