Hydrochloric Acid → 2-(3-Bromobenzyloxy)ethanol
Reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)[CH:14]=[CH:15][CH:16]=1.Cl>CCCCCCC>[Br:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH2:17][O:18][CH2:19][CH2:20][OH:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of DIBAL-H in heptane is added under an inert atmosphere to a cooled (−78° C.) solution of 2-(3-bromophenyl)-1,3-dioxolane in hexanes. The reaction mixture is stirred until no starting material is seen by TLC. Aqueous HCl (1N) is added to the reaction mixture while warming to room temperature. The product is extracted with EtOAc. Combined organic layers are dried over anhydrous MgSO4, and concentrated under reduced pressure to give 2-(3-bromobenzyloxy)ethanol.
Workup
- extractionThe product is extracted with EtOAc
- dry with materialCombined organic layers are dried over anhydrous MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ef7c7d306204474787bef04d9ea2bd32
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716529B2
Reaction notes
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