(4-Bromophenyl)boronic acid → HCID 66726624, compound

HRID 710357Notes

Reaction equation

HRID 710357 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15](I)[CH:14]=[CH:13][C:12]=3[O:18][CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Br:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:15]2[CH:14]=[CH:13][C:12]([O:18][CH3:19])=[C:11]([C:1]34[CH2:8][CH:7]5[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]5)[CH2:10]3)[CH2:2]4)[CH:16]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 66726367HCID 66726367, compound

Product 1

HCID 66726624HCID 66726624, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-(1-admantanyl)-4-iodo-1-methoxybenzene (0.19 g; 0.5 mmol) and 4-bromophenylboronic acid (0.1 g, 0.47 mmol) in 1,4-dioxane (10 ml) Pd(PPh3)4 (0.04 g) was added at 80° C., followed by the addition of the solution of NaHCO3 (0.2 g) in H2O (2 ml). The mixture was stirred at reflux for 2 h and the solvents were evaporated. The residue was diluted to 100 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4, filtered and the filtrate was evaporated to dryness to give The residue was purified by FCC (SiO2) to give the title product (0.08 g; 39%), as creamy gum. 1H-NMR (CDCl3) 1.77 (s, 6H); 2.07 (s, 3H); 2.12 (s, 6H); 3.86 (s, 3H); 6.92 (d, 1H, J=8.39 Hz); 7.34 (dd, 1H, J=2.42, 8.42 Hz), 7.38-7.42 (m, 3H); 7.50 (d, 2H, J=8.57 Hz).

Workup

  1. temperatureat reflux for 2 h
  2. customthe solvents were evaporated
  3. additionThe residue was diluted to 100 ml with EtOAc
  4. washwashed with H2O
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate was evaporated to dryness
  9. customto give The residue
  10. customwas purified by FCC (SiO2)

Sources & evidence

ORD record
ord-af384f37537641eb922e57ff38fcbe90
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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