Water → 5-Bromo-3,4-dihydro-8-hydroxy-3-methyl-1(2H)-naphthalenone

HRID 1274159Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 5-bromo-8-methoxy-3-methyl-1,2,3,4-tetrahydronaphthalen-1-one (32.2 g 0.12 mol) in DCM (400 mL) at 0° C. was added boron tribromide (119 mL of a 1.0 M solution in DCM, 0.12 mol) dropwise. The mixture was stirred at 5° C. for 1 h then water (50 mL) was added cautiously. The mixture was washed with water (3×200 mL) then the organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with hexane: DCM (100:0-1:1), to afford the phenol (23.5 g, 77%). 1H NMR (250 MHz, CDCl3) δ 1.18 (3H, d, J=6.1 Hz), 2.22-2.55 (3H, m), 2.69-2.77 (1H, m), 3.14-3.23 (1H, m), 6.74 (1H, d, J=8.9 Hz), 7.59 (1H, d, J=8.9 Hz), 12.54 (1H, s)

Workup

washThe mixture was washed with water (3×200 mL)
customthe organic layer was separated
dry with materialdried (Na2SO4)
customevaporated
customThe residue was chromatographed on silica gel
washeluting with hexane: DCM (100:0-1:1)

Sources & evidence

ORD record: ord-14d64b655e9d4b598047e87426d83a28
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156761

Reaction notes

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