Boron tribromide → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

HRID 1883265Notes

Reaction equation

C[O:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Intermediate 3, 10.7 g, 41.2 mmol) in CH2Cl2 (500 mL) at 0° C. was added BBr3 (49.5 mL, 1.0 M in CH2Cl2) via syringe pump over 10 min. The mixture was stirred at 0° C. for 2 h and was quenched with ice-H2O and extracted with Et2O (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (CH2Cl2) to give the title compound as a brown solid (7.6 g, 75%).

Workup

customwas quenched with ice-H2O
extractionextracted with Et2O (×3)
washThe combined organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record: ord-c26792f6ec9b4a26b3c5a26a47170c37
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759547B1

Reaction notes

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