Toluene → 2-(7-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene

HRID 1429339Notes

Reaction equation

HRID 1429339 reaction equation
[CH3:1][C:2]1([CH3:18])[C:14]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Br:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][C:24](Br)=[CH:25][CH:26]=2)[CH:21]=1.C1(C)C=CC=CC=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.O.C(COC)OC>[Br:19][C:20]1[CH:21]=[C:22]2[C:27]([CH:26]=[CH:25][C:24]([C:12]3[CH:11]=[CH:10][C:9]4[C:8]5[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:2]([CH3:1])([CH3:18])[C:14]=4[CH:13]=3)=[CH:23]2)=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 6253552,7-DibromonaphthaleneHCID 22348454(9,9-Dimethyl-9H-fluoren-2-yl)boronic acid

Product 1

HCID 585695012-(7-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluoreneYield 48%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

In argon atmosphere, a mixture of 16.65 g (69.9 mmol) of 9,9-dimethyl-9H-fluorene-2-ylboronic acid, 20.00 g (69.9 mmol) of 2,7-dibromonaphthalene, 4.04 g (3.50 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 200 ml of dimethoxyethane, and 106 g of a 2 M sodium carbonate aqueous solution was stirred at 85° C. for 9 h and left standing overnight. The reaction mixture was added with water and stirred at room temperature for one hour. After filtration, the filtrate was extracted with toluene. The organic phase was washed with water and then with a saturated saline solution and dried over sodium sulfate, and then the toluene was removed by distillation under reduced pressure. The obtained brown oily substance was purified by silica gel chromatography to obtain 13.4 g (yield: 48%) of 2-(7-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene.

Workup

  1. waitleft
  2. waitstanding overnight
  3. stirringstirred at room temperature for one hour
  4. filtrationAfter filtration
  5. extractionthe filtrate was extracted with toluene
  6. washThe organic phase was washed with water
  7. dry with materialwith a saturated saline solution and dried over sodium sulfate
  8. customthe toluene was removed by distillation under reduced pressure
  9. customThe obtained brown oily substance was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d82fd4f22f074e2ea132c149808685c0
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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