1,2-Dibromobenzene → 3-(2-Bromophenyl)-1-(3-(((2-tetrahydropyranyl)oxy)methyl)phenyl)-1-propanone

HRID 2259509Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:18])[CH:16]=[CH2:17])[CH:12]=[CH:13][CH:14]=1.[Br:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br.[Li+].[Cl-].[Li]OC(C)=O.O.O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:17][CH2:16][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:10]=1)=[O:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of the allylic alcohol of Example 1, Step 11, (30.14 g, 121 mmol), 1,2-dibromobenzene (16 mL), Pd(OAc)2 (830 mg), LiCl (5.38 g), LiOAc.2H2O (31.6 g), and Bu4NCl (67.96 g) in 240 mL of DMF was degassed and heated to 85° C. under N2 for 30 min and at 90° C. for 45 min. It was then added to ice and 25% aq. NH4OAc (2 L). The title ketone was extracted in EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:hexane 10:90; yield: 29.53 g (60%).

Workup

customwas degassed
additionIt was then added to ice and 25% aq. NH4OAc (2 L)
extractionThe title ketone was extracted in EtOAc
dry with materialdried over Na2SO4
custompurified by flash chromatography on silica with EtOAc:hexane 10:90

Sources & evidence

ORD record: ord-0f25bd43f76942dca77dfc49744755cc
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472964

Reaction notes

Loading…