4-Hydroxybenzaldehyde → HCID 86611514, compound

HRID 2224711Notes

Reaction equation

O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1.[C:18]([O-:21])([O-])=O.[K+].[K+].[C:24]([O-])(O)=O.[Na+]>CC(N(C)C)=O.O>[CH2:9]([C:8]1[CH:24]=[C:18]([O:21][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=2)[CH:3]=[CH:4][C:5]=1[CH:6]=[O:7])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-hydroxy benzaldehyde (4.22 g, 34.6 mmol) and 2,5-dibromopyridine (8.19 g, 34.6 mmol) in dimethylacetamide (100 mL) is added K2CO3 (11.95 g, 86.4 mmol) at RT. The reaction mixture is warmed to 130° C. for 8 h. The reaction mixture is then poured into H2O (200 mL) and saturated NaHCO3 (100 mL), extracted with EtOAc (3×200 mL), and then the combined extracts are washed with saturated NaHCO3, brine, dried over MgSO4, filtered, and concentrated. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 5% of ethyl acetate to 25% of ethyl acetate giving ethyl 4-(5-Bromo-pyridin-2-yloxy)-benzaldehyde (3.50 g, 36%) as a white solid. 1NMR (400 MHz, CDCl3) δ ppm: 9.96 (s, 1H), 8.23 (d, J=2.6 Hz, 1H), 7.93-7.90 (m, 2H), 7.83 (ds, J=2.6, 8.4 Hz, 1H), 7.27-7.24 (m, 2H), 6.92 (d, J=7.9 Hz, 1H); MS (ES): [M+H]+ found 277.7. Step 2 [4-(5-Bromo-pyridin-2-yloxy)-benzyl]-(3-methyl-butyl)-amine

Workup

extractionextracted with EtOAc (3×200 mL)
washthe combined extracts are washed with saturated NaHCO3, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
washeluted with hexanes with a gradient from 5% of ethyl acetate to 25% of ethyl acetate

Sources & evidence

ORD record: ord-a0294643267f43ed91013ce6a76c5462
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378448B2

Reaction notes

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