Isopropanol → 3-Fluoro-4'-(4-propylcyclohexyl)biphenyl-4-ol

HRID 1912235Notes

Reaction equation

[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[F:19][C:20]1[CH:25]=[C:24](Br)[CH:23]=[CH:22][C:21]=1[OH:27].C(=O)([O-])[O-].[K+].[K+].C(O)(C)C>O>[F:19][C:20]1[CH:25]=[C:24]([C:13]2[CH:12]=[CH:11][C:10]([CH:7]3[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]3)=[CH:15][CH:14]=2)[CH:23]=[CH:22][C:21]=1[OH:27]

Participants

Conditions

Temperature: 70 °C

Procedure

Dichlorobistriphenylphosphinepalladium (0.143 g) was added to a mixture of 4-(4-propylcyclohexyl)phenylboronic acid (10.0 g), 2-fluoro-4-bromophenol (7.76 g), potassium carbonate (11.2 g) and isopropyl alcohol (90 ml) under a stream of nitrogen, and the mixture was heated to reflux at 70° C. for 4 hours. The reaction mixture was poured into water, which was extracted with diethyl ether. The extract was washed with water three times and the solvent was distilled off. The residue was purified by silica gel-column chromatography (solvent: toluene/ethyl acetate=10/1 by volume), and then by recrystallization-filtration (solvent: toluene/heptane=0.5/2 by volume) to give colorless crystals of 3-fluoro-4′-(4-propylcyclohexyl)biphenyl-4-ol (7.0 g, GC purity: 95%).

Workup

temperaturethe mixture was heated
extractionwas extracted with diethyl ether
washThe extract was washed with water three times
distillationthe solvent was distilled off
customThe residue was purified by silica gel-column chromatography (solvent: toluene/ethyl acetate=10/1 by volume)
filtrationby recrystallization-filtration (solvent: toluene/heptane=0.5/2 by volume)

Sources & evidence

ORD record: ord-b94ad96e1ee6426fba0f01c98761210c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609207B2

Reaction notes

Loading…