Ethyl bromoacetate → Ethyl 2-(2-formyl-5-methoxyphenoxy)acetate

HRID 710330Notes

Reaction equation

HRID 710330 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=1[O:1][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5]

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 21476959Ethyl 2-(2-formyl-5-methoxyphenoxy)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-hydroxy-4-methoxybenzaldehyde (1 g; 6.58 mmol), BrCH2CO2Et (0.806 ml; 7.24 mmol) and K2CO3 (1 g, 7.24 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature. The mixture was diluted with EtOAc (100 ml) and H2O (100 ml). The organic layer was separated and dried over MgSO4, and filtrate evaporated, to give the product (1.29 g; 97%), as colourless solid. 1H-NMR (CDCl3) 1.28 (tr, 3H, J=7.11 Hz); 3.84 (s, 3H); 4.25 (q, 2H, J=7.14, 14.28 Hz); 4.69 (s, 2H); 6.30 (d, 1H, J=2.16 Hz); 6.58 (dd, 1H, J=1.77, 8.73 Hz); 7.83 (d, 1H, J=8.7 Hz); 10.36 (s, 1H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4, and filtrate
  3. customevaporated
  4. customto give the product (1.29 g; 97%)

Sources & evidence

ORD record
ord-15ffc691c5944afbac5f09602d1d7ed6
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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