Water → Ethyl 2-(4-formylphenyl)acetate
Reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[CH2:12]([O:14][C:15](=[O:18])[CH2:16]Br)[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C3C(=CC=CC=3)C=CC=2)C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1.C1COCC1>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:18])=[CH:5][CH:4]=1)=[O:2]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 65 °C
Procedure
A screw cap tube was loaded with (4-formylphenyl)boronic acid (450 mg, 3 mmol), ethylbromoacetate (0.22 mL, 2 mmol), potassium carbonate (830 mg, 6 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), tri-1-naphtylphosphine (62 mg, 0.15 mmol), H2O (0.5 mL), and THF (4.5 mL). The mixture was degased with nitrogen for 5 minutes and then heated to 65° C. for 18 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (50 mL) and washed with water (2×50 mL). The organic phase was filtered through a phase separator and the solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-20% EtOAc in isohexane, to yield ethyl 2-(4-formylphenyl)acetate as colourless oil (327 mg, 57%).
Workup
- customA screw cap tube
- customThe mixture was degased with nitrogen for 5 minutes
- temperatureThe reaction was cooled to room temperature
- additiondiluted with ethyl acetate (50 mL)
- washwashed with water (2×50 mL)
- filtrationThe organic phase was filtered through a phase separator
- customthe solvent was removed in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with 0-20% EtOAc in isohexane
Sources & evidence
- ORD record
- ord-c230cc0297ad497a959c38b86609fb08
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199980B2
Reaction notes
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