1,3-Dibromobenzene → HCID 71138690, compound

HRID 1852930Notes

Reaction equation

HRID 1852930 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH:9]12[O:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][NH:11][CH2:10]2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:4]1[CH:3]=[C:2]([N:11]2[CH2:10][CH:9]3[O:16][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 79271,3-DibromobenzeneHCID 634876Binap, (A+-)-HCID 120692318-Oxa-3-azabicyclo[3.2.1]octaneHCID 23676156Sodium t-butoxide

Product 1

HCID 71138690HCID 71138690, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,3-dibromobenzene (242 μL, 2.00 mmol), 8-oxa-3-azabicyclo[3.2.1]octane (226 mg, 2.00 mmol), Pd2(dba)3 (45.8 mg, 0.0500 mmol), rac-BINAP (96.3 mg, 0.150 mmol) and NaOtBu (231 mg, 2.40 mmol) in toluene was heated at 80° C. for 13 hours under nitrogen. After cooling to room temperature, the mixture was diluted with DCM and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=9:1) to afford desired product (361 mg, 67.3%) as colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through a Celite pad
  3. concentrationThe combined filtrate and washings were concentrated
  4. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=9:1)

Sources & evidence

ORD record
ord-8940b06518cd42979fd2e02a419fc55b
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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