4-Bromo-2-(1-hydroxy-2-methylpropyl)phenol → 1-(5-Bromo-2-hydroxyphenyl)-2-methylpropan-1-one

HRID 1711789Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([OH:13])[CH:10]([CH3:12])[CH3:11])[CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9](=[O:13])[CH:10]([CH3:11])[CH3:12])[CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-Bromo-2-(1-hydroxy-2-methylpropyl)phenol (4.88 g, 19.9 mmol) was dissolved in DCM (50 mL) then manganese dioxide (2.44 g, 23.8 mmol) was added. After stirring for about 2 h at ambient temperature another portion of manganese dioxide (2.44 g, 23.8 mmol) was added then the mixture was heated to about 40° C. After about 2 d the mixture was filtered then evaporated and the residue purified by flash chromatography on silica gel with 9:1 Heptane/EtOAc as an eluent to give the title compound (0.82 g, 17%): LC/MS (Table 1, Method a) Rt, =3.38 min; MS m/z: 241.1 (M−H)−.

Workup

additionwas added
filtrationAfter about 2 d the mixture was filtered
customthen evaporated
customthe residue purified by flash chromatography on silica gel with 9:1 Heptane/EtOAc as an eluent

Sources & evidence

ORD record: ord-f53cc1705ad14a00a86ea024727b0fa1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790741B2

Reaction notes

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