Boron tribromide → 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-one

HRID 1095275Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:26])[CH:6]=C(C1C=CC([N+]([O-])=O)=CC=1)[O:8]2.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[C:4]([C:5](=[O:26])[CH3:6])=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 8 (71 mg, 0.2 mmol) in CH2Cl2 (5 mL) was added a 1M solution of boron tribromide (0.4 mL, 0.4 mmol) in CH2Cl2 at −78° C. The solution was stirred for an additional 2 h and at −20° C. for 5 h then quenched with water (10 mL). The precipitate was collected by filtration and recrystallized from CH2Cl2 to afford crude product 5 (30 mg, 46%). 1H NMR (400 MHz, DMSO) δ 3.93 (s, 3H), 7.01 (s, 1H), 7.21 (s, 1H), 8.38-8.39 (m, 4H).

Workup

customthen quenched with water (10 mL)
filtrationThe precipitate was collected by filtration
customrecrystallized from CH2Cl2

Sources & evidence

ORD record: ord-0f4a366b605d43819bc114768dee489b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138165B2

Reaction notes

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