Hydrochloric Acid → 5-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol

HRID 2280614Notes

Reaction equation

[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH2:2]1.C([Li])CCC.[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2.Cl>O1CCCC1>[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH:2]1[S:3][CH2:4][CH2:5][CH2:6][S:1]1)([OH:22])[CH2:17][CH2:16]2

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 1,3-dithiane (11.96 g, 99 mmol) in anhydrous tetrahydrofuran (100 mL) at −30° C. was treated dropwise over 10 min with n-butyllithium (2.5M in hexanes, 38.4 mL, 96 mmol) followed by stirring at −15° C. for 2 h. The solution was then treated with a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (15 g, 71.1 mmol) in anhydrous tetrahydrofuran (250 mL) over 1 h, maintaining the temperature between −9° C. and 2° C. The mixture was then allowed to set in the refrigerator at 2-8° C. for 18 h. The solution was concentrated in vacuo to afford a maroon oil, which was treated with 1 N hydrochloric acid solution and extracted with ether. The ether layer was extracted with saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo to afford an amber oil (23.55 g).

Workup

temperaturemaintaining the temperature between −9° C. and 2° C
waitto set in the refrigerator at 2-8° C. for 18 h
concentrationThe solution was concentrated in vacuo
customto afford a maroon oil, which
extractionextracted with ether
extractionThe ether layer was extracted with saturated sodium chloride solution
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4da8b961396b41438095f60fc36f0b12
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139536B2

Reaction notes

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