Triethylamine → 1,1'-(Naphtho[1,2-b]thiophene-2,7-diyl)bis(2-bromoethanone)

HRID 1521801Notes

Reaction equation

[S:1]1[C:5]([C:6](=[O:10])[CH:7](Br)[Br:8])=[CH:4][C:3]2[CH:11]=[CH:12][C:13]3[C:18]([C:2]1=2)=[CH:17][CH:16]=[C:15]([C:19](=[O:23])[CH:20](Br)[Br:21])[CH:14]=3.P([O-])(OCC)OCC.C(N(CC)CC)C>C1COCC1>[S:1]1[C:5]([C:6](=[O:10])[CH2:7][Br:8])=[CH:4][C:3]2[CH:11]=[CH:12][C:13]3[C:18]([C:2]1=2)=[CH:17][CH:16]=[C:15]([C:19](=[O:23])[CH2:20][Br:21])[CH:14]=3

Participants

Conditions

Temperature: 0 °C

Procedure

1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)bis(2,2-dibromoethanone) (10b) (180 g, 310 mmol) obtained as above was dissolved in 500 ml of THF and the solution was cooled to 0° C. A mixture of diethyl phosphite (80 ml, 620 mmol) and triethylamine (86 ml, 210 mmol) in 50 ml THF was added dropwise to the solution which was kept on an ice bath. After the addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hr. The volume of THF was reduced by rotary evaporation to obtain a solid residue which was washed with pentane to afford 1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)bis(2-bromoethanone) as a brown solid (10c) (110 g, 84%).

Workup

additionwas added dropwise to the solution which
customwas kept on an ice bath
additionAfter the addition
customthe ice bath was removed
customThe volume of THF was reduced by rotary evaporation
customto obtain a solid residue which
washwas washed with pentane

Sources & evidence

ORD record: ord-eb899aec34cb456db00fd19261adb2cf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073942B2

Reaction notes

Loading…