Water → 4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-oxo-1-pentene

HRID 4463

Reaction equation

[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]([CH3:19])[C:13]([O:17]C)=[CH:14][CH2:15]O)=[CH:9][CH:8]=2)=[C:4]([F:24])[CH:3]=1.O>C(Cl)Cl>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]([CH3:19])[C:13](=[O:17])[CH:14]=[CH2:15])=[CH:9][CH:8]=2)=[C:4]([F:24])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 30 ml of 35% HClO4 and 15 ml CH2Cl2 at 0° C. was added 3.0 g (7.55 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-penten-1-ol in 15 ml CH2Cl2. The mixture was stirred at 0° C. for 45 min, then poured into water and extracted with ether. The combined ether extracts were washed with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC, eluting with 95:5 hexane:acetone, to give 1.9 g (69%) of the product as a clear, colorless oil. Structure was established on the basis of IR and NMR analysis. Calc: C, 55.91; H, 3.86. Found: C, 56.84, H, 4.00.

Workup

extractionextracted with ether
washThe combined ether extracts were washed with water
dry with materialdried over MgSO4
customthe solvent was removed by rotary evaporation
customThe residue was purified by HPLC
washeluting with 95:5 hexane

Sources & evidence

ORD record: ord-fd27dcb7b04c492084da2155de44a546
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725683

Linked notes

Loading…