Borane → (3-Bromo-4-methoxyphenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].B>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:5][OH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 9.8 g (42 mmol) of 3-bromo-4-methoxybenzoic acid in THF (100 mL) was added 1M solution of borane in THF (130 mL) at r.t. under nitrogen. The resulting solution was then heated at 75° C. for 30 min. The reaction mixture was then cooled to r.t. and MEOH (0.5 mL) was slowly added. The mixture was concentrated and successively treated with MEOH (0.5 mL), evaporated (2×) and finally triturated with Et2O and filtered to yield the title product as a solid, m.p.: 49°-54° C.
Workup
- temperatureThe reaction mixture was then cooled to r.t.
- additionMEOH (0.5 mL) was slowly added
- concentrationThe mixture was concentrated
- additionsuccessively treated with MEOH (0.5 mL)
- customevaporated (2×)
- customfinally triturated with Et2O
- filtrationfiltered
Sources & evidence
- ORD record
- ord-59706ef6b75247a491c5195bc05c918d
- Source dataset
- uspto-grants-1994_01
- Patent number
- US05281720
Reaction notes
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