Sodium Carbonate → 9-(3-Bromophenyl)phenanthrene

HRID 1429322Notes

Reaction equation

HRID 1429322 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:20]=[C:21](I)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(COC)OC>[Br:18][C:19]1[CH:24]=[C:23]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 117757049-Phenanthracenylboronic acid

Product 1

HCID 221380359-(3-Bromophenyl)phenanthreneYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

In argon atmosphere, a mixture of 31.4 g (141 mmol) of 9-phenanthreneboronic acid, 40.0 g (141 mmol) of 3-bromoiodobenzene, 3.30 g (2.83 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 50 ml of dimethoxyethane and 212 ml of a 2 M sodium carbonate aqueous solution, and the mixture was refluxed under stirring for 4 h. After the reaction, the reaction mixture was added with toluene and washed with water. The organic phase was dried over sodium sulfate, and then toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 34.7 g (yield: 74%) of 9-(3-bromophenyl)phenanthrene.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter the reaction
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customtoluene was removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-515554f0bb124ebc9cdfcbc15dd1be57
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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