Hydrochloric Acid → 4-(3-Hydroxypropoxy)-3-(trifluoromethyl)phenylboronic acid
Reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]([OH:20])[OH:19])=[CH:14][C:13]=1[C:21]([F:24])([F:23])[F:22].Cl>>[OH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]([OH:19])[OH:20])=[CH:14][C:13]=1[C:21]([F:24])([F:22])[F:23]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
4-(3-(Tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenylboronic acid (30.6 g) was added to hydrochloric acid (1M in MeOH) and the mixture was heated at 50° C. for 40 minutes. Solvent and HCl were then removed under reduced pressure and residue (20.3 g) was used for next step without further purification. Proton NMR indicates 2 sets of product peaks assumed to be monomer and dimer or trimer. 1H NMR (CDCl3 (0.7 ml)+CD3OD (0.2 ml)) δ: 7.7-8.0 (2xd and 2xs, 2H), 7.0 (2xd, 1H), 4.22 (t, 2H), 3.86 (t, 2H), 3.48 (tt, 2H).
Workup
- customSolvent and HCl were then removed under reduced pressure and residue (20.3 g)
- customwas used for next step without further purification
Sources & evidence
- ORD record
- ord-d730038a0b2441b9b4d587e70bbe40ad
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026236B2
Reaction notes
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