Boron tribromide → 2-(4-Methoxyphenoxy)-5-propylphenol

HRID 625999Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.B(Br)(Br)Br>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:4]2[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][CH3:11])=[CH:8][C:3]=2[OH:2])=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 247861922-Methoxy-1-(4-methoxyphenoxy)-4-propylbenzene

Product 1

HCID 591912062-(4-Methoxyphenoxy)-5-propylphenolYield 32%

Procedure

According to the procedure of example 5 (b) except substituting 2-fluoro-6-(2-methoxy-4-propylphenoxy)pyridine for 2-methoxy-1-(4-methoxyphenoxy)-4-propylbenzene (0.18 mmol; 50 mg) and adding 4 equivalents (0.735 mmol; 735 μl) of boron tribromide, the title compound was prepared in 32% yield (0.06 mmol; 15 mg) after purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—20/80).

Workup

customafter purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—20/80)

Sources & evidence

ORD record: ord-2e8d08de7c4746b39d9a71cd80dc150f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309179B2

Reaction notes

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