1,4-Dibromobenzene → 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1893078Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.[O:10]1[C:14]2([CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1.[NH4+].[Cl-]>C1COCC1>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([C:17]2([OH:20])[CH2:18][CH2:19][C:14]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:15][CH2:16]2)=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 22.5 °C

Procedure

Magnesium (0.60 g, 24.6 mmol) and THF (5 ml) were added to 2-neck flask, and the reaction was initiated with addition of small amount of THF (25 ml) a solution including 1,4-dibromobenzene (5.30 g, 22.4 mmol). Then, the remaining THF solution including 1,4-dibromobenzene was slowly added dropwise with maintaining at 20-25° C. and was stirred for 2 hours. THF solution (8 ml) of 1,4-Dioxaspiro[4.5]decan-8-one (2.60 g, 17.0 mmol) was added slowly dropwise with maintaining 10-15° C., warmed to a room temperature and then stirred for 24 hours at a room temperature. The reacting solution was poured to NH4Cl aqueous solution (50 ml), and extracted by toluene (50 ml×3 time). The organic layer was washed by distilled water (20 ml×2 times) and concentrated under reduced pressure concentrate to obtain 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-ol (9.30 g).

Workup

additionwas slowly added dropwise
temperaturewith maintaining 10-15° C.
temperaturewarmed to a room temperature
stirringstirred for 24 hours at a room temperature
extractionextracted by toluene (50 ml×3 time)
washThe organic layer was washed
distillationby distilled water (20 ml×2 times)
concentrationconcentrated under reduced pressure
concentrationconcentrate

Sources & evidence

ORD record: ord-7389e36a8e1e474a8a492189c930adfa
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08512598B2

Reaction notes

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