3'-Hydroxyphenylacetic acid → [3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid

HRID 1969014Notes

Reaction equation

HRID 1969014 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[C:17]([CH:20]=1)[CH:18]=[O:19].[H-].[Na+]>CN(C=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[C:17]([CH:18]=[O:19])[CH:20]=1

Participants

5

Reactant 3

HCID 121223'-Hydroxyphenylacetic acidHCID 24758Sodium hydrideHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 58237510[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-Hydroxyphenylacetic acid (1.34 g, 8.8 mmol) and 5-bromo-2-fluorobenzaldehyde (1.78 g, 8.8 mmol) were combined in DMF (30 mL) at room temperature. Sodium hydride (60% in mineral oil; 0.72 g, 18.0 mmol) was added, and the reaction was stirred at 70° C. for 2 hours. Aqueous work-up yielded the title compound.

Sources & evidence

ORD record
ord-1b02aa2f91f44396b82a40aac6e06efa
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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