Sodium Carbonate → HCID 68900889, compound

HRID 735305Notes

Reaction equation

HRID 735305 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O.COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][C:18]=3[F:20])[CH:3]=2)[CH:8]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 6405912,6-DibromonaphthaleneHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 68900889HCID 68900889, compoundYield 17.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dibromonaphthalene (12.49 g, 43.7 mmol), 2,4-difluorobenzeneboronic acid (3.44 g, 21.8 mmol), sodium carbonate (4.63 g, 45.7 mmol), palladium acetate (245 mg, 1.09 mmol) and tri-o-tolylphosphine (667 mg, 2.19 mmol) in water (15 mL) and ethylene glycol dimethyl ether (90 mL) was degassed and heated to 80° C. overnight. The cooled reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with isohexane, to give 2-bromo-6-(2,4-difluorophenyl)naphthalene (1.24 g, contains 10% 2,6-dibromonaphthalene). 1H NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.93 (1H, s), 7.82 (1H, d, J=8.5 Hz), 7.75 (1H, d, J=8.6 Hz), 7.62 (2H, dd, J=8.4, 31.8 Hz), 7.50 (1H, m), 7.04-6.91 (2H, m).

Workup

  1. customwas degassed
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica
  9. washeluting with isohexane

Sources & evidence

ORD record
ord-690cdbc5f5fa402990a4cc7c24bb6239
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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