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

HRID 1991920
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HRID 1991920 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6212Chloroform용매
HCID 8028Tetrahydrofuran용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-95c3ae9386b44e179334059e42f7411a
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07645910B2

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