Hydrochloric Acid → 3-Bromo-2-hydroxybenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Cl-].[Mg+2].[Cl-].[CH2:12]=[O:13].C(N(CC)CC)C.Cl>C(#N)C>[Br:1][C:2]1[C:3]([OH:8])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:12]=[O:13]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
20.0 g (115.6 mmol) of 2-bromophenol are introduced into 500 ml of dry acetonitrile. 16.84 g (176.87 mmol) of dry magnesium chloride, 23.4 g of paraformaldehyde granules and 41.9 ml (300.6 mmol) of triethylamine are added. The reaction mixture is heated under reflux for 4 h and, after cooling to 0° C., 300 ml of 2N hydrochloric acid are added. The aqueous phase is extracted three times with 200 ml of diethyl ether each time. The organic phase is dried over magnesium sulphate, and the solvent is removed in vacuo. 24 g (64% of theory, 62% pure according to HPLC) of the title compound are isolated and reacted further without further purification.
Workup
- temperatureThe reaction mixture is heated
- temperatureunder reflux for 4 h
- extractionThe aqueous phase is extracted three times with 200 ml of diethyl ether each time
- dry with materialThe organic phase is dried over magnesium sulphate
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-cba3f06db2ae4e49bc2a7da335f80031
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977485B2
Reaction notes
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