Potassium Carbonate → 4-(2-Acetoxyethoxy)-3-fluorobenzaldehyde

HRID 80006

Reaction equation

HRID 80006 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].[C:17]([O:20][CH2:21][CH2:22]Br)(=[O:19])[CH3:18]>CC(C)=O.C(OCC)C>[C:17]([O:20][CH2:21][CH2:22][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 871794064-(2-Acetoxyethoxy)-3-fluorobenzaldehydeYield 51%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-fluoro-4-hydroxybenzaldehyde (2.0 g, 14.3 mmol), K2CO3 (5.92 g, 42.8 mmol) and 2-bromoethyl acetate (4.77 g, 28.5 mmol) in acetone (30 mL) is stirred at 55° C. for 24 h before it is diluted with diethyl ether (150 mL) and washed with water (3×50 mL). The organic extract is dried over MgSO4 and concetrated. The remaining residue is chromatographed on silica gel to give the title aldehyde (1.65 g) as a colourless oil. 1H NMR (CDCl3): δ 9.85 (s, 1H), 7.64-7.58 (m, 2H), 7.07 (t, J=8.2 Hz, 1H), 4.49-4.45 (m, 2H), 4.35-4.30 (m, 2H), 2.10 (s, 3H).

Workup

  1. washwashed with water (3×50 mL)
  2. extractionThe organic extract
  3. dry with materialis dried over MgSO4
  4. customThe remaining residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f4d6cc8608e242818de875804781c99a
Source dataset
uspto-grants-2014_09
Patent number
USRE045174E1

Linked notes

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