Tetrahydrofuran → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-bromonaphthalene

HRID 1991921Notes

Reaction equation

HRID 1991921 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](B4OCC(C)(C)CO4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.FC(F)(F)S(O[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([Br:43])[CH:39]=2)[CH:34]=1)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1COCC1>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:1]12([C:11]3[CH:12]=[C:13]([C:33]4[CH:34]=[C:35]5[C:40](=[CH:41][CH:42]=4)[CH:39]=[C:38]([Br:43])[CH:37]=[CH:36]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 66937976(3-(1-Adamantyl)-4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Product 1

HCID 591298026-[3-(1-Adamantyl)-4-methoxyphenyl]-2-bromonaphthaleneYield 24%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

[3-(1-adamantyl)-4-methoxyphenyl]-5,5-dimethyl-1,3,2-dioxaborinane (100 mg, 0.28 mmol), 6-bromo-2-naphthalenyl trifluoromethanesulphonate (67 mg, 0.19 mmol), K3PO4 (160 mg, 0.75 mmol), THF (2 ml) and H2O (0.4 ml) were introduced in a Schlenk tube. The reaction mixture was deoxygenated (3 froze/thaw cycles). Next, Pd(PPh3)4 (11 mg, 0.009 mmol) was added and the mixture was again deoxygenated (2 froze/thaw cycles). After heating at reflux for 17 h, the mixture was diluted in toluene (5 ml) while it was still hot. The solution was filtered through celite and it was washed with hot toluene (2×5 ml). The joined organic phases were washed with hot H2O (2×5 ml). The organic phase was evaporated and a crude (59 mg) was obtained, which was recrystallized with the minimum volume of toluene at reflux (0.55 ml), giving the title compound (20 mg, 24%) as a pale yellow powder. The spectroscopic data coincide with those of the Example 4.

Workup

  1. customThe reaction mixture was deoxygenated (3 froze/thaw cycles)
  2. customthe mixture was again deoxygenated (2 froze/thaw cycles)
  3. temperatureAfter heating
  4. temperatureat reflux for 17 h
  5. additionthe mixture was diluted in toluene (5 ml) while it
  6. filtrationThe solution was filtered through celite and it
  7. washwas washed with hot toluene (2×5 ml)
  8. washThe joined organic phases were washed with hot H2O (2×5 ml)
  9. customThe organic phase was evaporated
  10. customa crude (59 mg) was obtained
  11. customwhich was recrystallized with the minimum volume of toluene
  12. temperatureat reflux (0.55 ml)

Sources & evidence

ORD record
ord-3850f3e7145c4607a0f806997b5766be
Source dataset
uspto-grants-2010_01
Patent number
US07645910B2

Reaction notes

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