Boron tribromide → 6-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421255Notes

Reaction equation

[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=2)=[C:5]([O:21]C)[CH:4]=1)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:21])[C:6]2[CH:7]=[CH:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=3)[C:10]=2[CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole (D10) (180 mg, 0.60 mmol) in dichloromethane (6 mL) at −78° C. was added boron tribromide (1 M solution in dichloromethane, 2.5 mL, 2.5 mmol). The reaction mixture was allowed to warm to 0° C. and then quenched by the addition of water and dichloromethane. The solution was neutralised by the addition of dilute sodium hydrogen carbonate solution. The organic phase was separated and then the aqueous phase re-extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was purified by MDAP to yield the title compound (E6), (8 mg).

Workup

customquenched by the addition of water and dichloromethane
additionThe solution was neutralised by the addition of dilute sodium hydrogen carbonate solution
customThe organic phase was separated
extractionthe aqueous phase re-extracted with ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated at reduced pressure
customThe product was purified by MDAP

Sources & evidence

ORD record: ord-b2256c0ba64f4d41bbed2ab04154f8ef
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956083B2

Reaction notes

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