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

HRID 1962335

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-3abd8d3f43fc41eab4f5e0068c4e9ec2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415351B2

Linked notes

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