Hydrochloric Acid → 4-(3-Hydroxypropoxy)-3-(trifluoromethyl)phenylboronic acid

HRID 2079530Notes

Reaction equation

HRID 2079530 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

Reactant 2

HCID 313Hydrochloric AcidHCID 576575864-(3-(Tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenylboronic acid

Product 1

HCID 576575354-(3-Hydroxypropoxy)-3-(trifluoromethyl)phenylboronic acid

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 (2×d and 2×s, 2H), 7.0 (2×d, 1H), 4.22 (t, 2H), 3.86 (t, 2H), 3.48 (tt, 2H).

Workup

  1. customSolvent and HCl were then removed under reduced pressure and residue (20.3 g)
  2. customwas used for next step without further purification

Sources & evidence

ORD record
ord-d027f4506d084d1b84f108f7d8399ff3
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

Loading…