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Potassium Phosphate, Tribasic → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-bromonaphthalene

HRID 1991920
Notes
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Reaction equation

HRID 1991920 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](B(O)O)[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:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([Br:38])[CH:34]=2)[CH:29]=1)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[K+].[Br-]>C(Cl)(Cl)Cl.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.C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([C:28]4[CH:29]=[C:30]5[C:35](=[CH:36][CH:37]=4)[CH:34]=[C:33]([Br:38])[CH:32]=[CH:31]5)[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 253877Potassium BromideHCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 231485923-(1-Adamantyl)-4-methoxyphenylboronic acid

Product 1

HCID 591298026-[3-(1-Adamantyl)-4-methoxyphenyl]-2-bromonaphthalene

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6212ChloroformSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

3-(1-adamantyl)-4-methoxyphenylboronic acid (150 mg, 0.32 mmol), 6-bromo-2-naphtalenyl trifluoromethanesulphonate (93 mg, 0.26 mmol), K3PO4 (222 mg, 1.05 mmol), KBr (34 mg, 0.29 mmol) and THF (2 ml) were introduced into a Schlenk tube. Next, the reaction mixture was deoxygenated (3 froze/thaw cycles). Next, Pd(PPh3)4 (15 mg, 0.013 mmol) was added and the mixture was again deoxygenated (2 froze/thaw cycles). After heating at reflux for 18 h, the mixture was brought at room temperature and was diluted with CHCl3 (5 ml). The solution was filtered through celite and washings with CHCl3 (2×5 ml) were carried out. The evaporation of the joined organic phases gave a residue which was redissolved in CHCl3 (5 ml) and washed with H2O (2×5 ml). The organic phase was dried with Na2SO4 and after evaporation to dryness, a crude was obtained (97 mg) which was recrystallized with the minimum volume of toluene at reflux. The title compound was obtained (68 mg, 58%) as a pale yellow powder. IR (KBr) 2900, 2847, 1600, 1489, 1456, 1442, 1262, 1237, 1178, 1142, 1103, 1061, 1026, 877, 809 y 470. M/Z (El) 448 [M+ (81Br), 76%] y 446 [M+ (79Br), 100].

Workup

  1. customNext, the 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 18 h
  5. customwas brought at room temperature
  6. additionwas diluted with CHCl3 (5 ml)
  7. filtrationThe solution was filtered through celite and washings with CHCl3 (2×5 ml)
  8. customThe evaporation of the joined organic phases
  9. customgave a residue which
  10. washwashed with H2O (2×5 ml)
  11. dry with materialThe organic phase was dried with Na2SO4
  12. customafter evaporation to dryness
  13. customa crude was obtained (97 mg) which
  14. customwas recrystallized with the minimum volume of toluene
  15. temperatureat reflux

Sources & evidence

ORD record
ord-95c3ae9386b44e179334059e42f7411a
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07645910B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes