Cesium fluoride → Dimethyl 3,3'-(naphthalene-2,7-diyl)dibenzoate

HRID 1484215Notes

Reaction equation

HRID 1484215 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6](Br)=[CH:7][CH:8]=2)[CH:3]=1.[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16].[F-].[Cs+]>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>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[C:15]([O:14][CH3:13])=[O:16])[CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=1)[C:15]([O:14][CH3:13])=[O:16]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 6253552,7-DibromonaphthaleneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 71283629Dimethyl 3,3'-(naphthalene-2,7-diyl)dibenzoateYield 72%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a 250 mL Schlenk flask, 2,7-dibromonaphthalene (2.00 g, 6.99 mmol), 3-(methoxycarbonyl)phenylboronic acid (3.15 g, 17.48 mmol), CsF (4.00 g) and Pd(PPh3)4 (200 mg) were added. The flask was connected to a Schlenk line and evacuated of air then refilled with nitrogen. 150 mL of 1,2-dimethoxyethane (DME) was degassed (two hours) and added to the flask through a canula. The flask was equipped with a water condenser and refluxed under nitrogen for 2 days. The solvent was removed on a rotary evaporator. 100 mL of H2O was added and then extracted with CHCl3. The organic phase was dried with MgSO4. After removal of the CHCl3 solvent, the crude product was re-crystallized from the mixture solvent of ethyl acetate and hexane (v/v=1:9) to give a pure product with a yield of 72% (2.0 g) based on 2,7-dibromonaphthalene. 1H NMR (300 MHz, DMSO-d6): δ 3.92 (s, 6H), 7.70 (t, 2H), 7.93 (d, 2H), 8.01 (d, 2H), 8.13 (m, 4H), 8.39 (m, 2H), 8.45 (d, 2H).

Workup

  1. customThe flask was connected to a Schlenk
  2. customline and evacuated of air
  3. additionthen refilled with nitrogen
  4. custom150 mL of 1,2-dimethoxyethane (DME) was degassed (two hours)
  5. additionadded to the flask through a canula
  6. customThe flask was equipped with a water condenser
  7. temperaturerefluxed under nitrogen for 2 days
  8. customThe solvent was removed on a rotary evaporator
  9. addition100 mL of H2O was added
  10. extractionextracted with CHCl3
  11. dry with materialThe organic phase was dried with MgSO4
  12. customAfter removal of the CHCl3 solvent
  13. customthe crude product was re-crystallized from the mixture solvent of ethyl acetate and hexane (v/v=1:9)
  14. customto give a pure product with a yield of 72% (2.0 g)

Sources & evidence

ORD record
ord-a3f12c3fdd674e57810d9cc9e2172e5c
Source dataset
uspto-grants-2016_08
Patent number
US09421514B2

Reaction notes

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