Water → Methyl 2-(3-bromo-2-hydroxyphenyl)acetate
Reaction equation
C(N)(C)(C)C.[Br:6]Br.[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17].O>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Br:6])[C:9]=1[OH:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -30 °C
Procedure
To a solution of tert-butylamine (1.74 mL, 16.4 mmol, 1.50 eq.) in toluene (54 mL), bromine (0.47 mL, 9.2 mmol, 0.84 eq.) was added dropwise at −30° C. The mixture was stirred at −30° C. for 1 hour then cooled down to −78° C. and a solution of methyl 2-(2-hydroxyphenyl)acetate (1.82 g, 11.0 mmol, 1.00 eq.) in DCM (10 mL) was slowly added. The resulting mixture was stirred at r.t. for 18 hours. Water was added and the layers were separated. The aq. phase was extracted with DCM (2×). The comb. org. layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated to give (3-bromo-2-hydroxy-phenyl)-acetic acid methyl ester as a pale yellow oil that solidified upon standing.
Workup
- temperaturethen cooled down to −78° C.
- stirringThe resulting mixture was stirred at r.t. for 18 hours
- customthe layers were separated
- extractionThe aq. phase was extracted with DCM (2×)
- dry with materiallayers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by prep
- customHPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated
Sources & evidence
- ORD record
- ord-8d16e606259949efaca37c36a58b0e85
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255090B2
Reaction notes
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