4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

HRID 416290Notes

Reaction equation

HRID 416290 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][CH2:8][CH2:9]Br.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1>CN(C=O)C>[Br:7][CH2:8][CH2:9][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 2627064-(2-Bromoethoxy)BenzaldehydeYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of K2CO3 (4.52 g, 32.7 mmol), 1,2-dibromoethane (10.6 ml, 122.8 mmol) in DMF (12 mL) was added a solution of 4-hydroxybenzaldehyde (1.0 g, 8.2 mmol) in DMF (3 mL) at 0° C. The mixture was stirred at room temperature for 18 h., filtered and evaporated. The residue was purified by silica gel column chromatography with gradient of EtOAc-hexane (increasing percentage of EtOAc from 20 to 25%) to afford the title compound (1.21 g, 64% yield). 1H NMR: (CDCl3) δ (ppm): 9.88 (s, 1H), 7.84 (d, J=8.0 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 4.38 (t, J=6 Hz, 2H), 3.67 (t, J=6 Hz, 2H). LRMS (ESI): (calc.) 227.9, 229.9; (found) 229.1, 231.3 (MH)+.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by silica gel column chromatography with gradient of EtOAc-hexane (increasing percentage of EtOAc from 20 to 25%)

Sources & evidence

ORD record
ord-4704bd0f9cd94f118213a271593066dc
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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