Ethanol → 4-(5-Bromo-2-pyridinyl)phenol

HRID 423522Notes

Reaction equation

HRID 423522 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>C1(C)C=CC=CC=1.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>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 27343604-Hydroxyphenylboronic acid

Product 1

HCID 1363884624-(5-Bromo-2-pyridinyl)phenolYield 24%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

4-(5-Bromo-2-pyridinyl)phenol (0.25 g, 24%) was prepared as a white solid from (4-hydroxyphenyl)boronic acid (0.60 g, 4.22 mmol), 2,5-dibromopyridine (1.0 g, 4.22 mmol), 2M Na2CO3 (6 mL), EtOH (2 mL) and Pd(PPh3)4 (0.15 g, 0.13 mmol) in toluene (4 mL) in a manner similar to Example 1, Step 1, except the reaction was heated overnight. 1H NMR (400 MHz, CDCl3): δ 8.68 (d, 1H, J=2.2 Hz), 7.90-7.80 (m, 3H), 7.56 (d, 1H, J=8.5 Hz), 6.92 (d, 2H, J=8.5 Hz), 5.18 (bs, 1H); LRMS (ESI), m/z 250/252 (M+H).

Workup

  1. temperaturewas heated overnight

Sources & evidence

ORD record
ord-99f39151233e4884ac14a1fe283db327
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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