4-Bromophenacyl bromide → HCID 178444622, compound

HRID 1813594Notes

Reaction equation

HRID 1813594 reaction equation
C#CCCCCC=O.Brc1ccc(C(=O)CBr)cc1>C1COCCN1.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=C([C-]=C1)C2=CC=CC=N2.C1=CC=C([C-]=C1)C2=CC=CC=N2.[Ir+3].CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(Br)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(Br)cc1

Participants

8

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 79372,6-LutidineHCID 11355455Hept-6-ynal

Product 2

HCID 178444622HCID 178444622, compoundHCID 178444623HCID 178444623, compound

Reagents, catalysts & solvents 3

HCID 8083MorpholineCatalystHCID 11388194Ir(ppy)3CatalystHCID 6228DimethylformamideSolvent5×

Conditions

Temperature
22 °C

Workup

  1. aliquot4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  2. addition4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  3. additionchiral resolving regent (150 mM in DCM, 40 uL)
  4. additionCuI with DIPEA (400 mM in ACN) 40 uL
  5. additioninternal standard 1-phenylprop-2-yn-1-ol (4) (25 mM in ACN) 40 uL
  6. stirringNo procedure recorded
  7. aliquotAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate
  8. additionAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate and diluted with 190 uL ACN before the IM-MS analysis

Sources & evidence

ORD record
ord-e20c5df6d3e7450ca15ad189279f3ae6
Source dataset
Dataset from `Ultra-high-throughput mapping of the chemical space of asymmetric catalysis enables accelerated reaction discovery`

Reaction notes

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