Boron tribromide → HCID 59191384, compound

HRID 626015Notes

Reaction equation

HRID 626015 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[O:20]C)[N:3]=1.B(Br)(Br)Br>>[F:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([F:17])([F:18])[F:19])=[CH:11][C:10]=2[OH:20])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59191408HCID 59191408, compound

Product 1

HCID 59191384HCID 59191384, compoundYield 75%

Procedure

According to the procedure of example 5 (b) except substituting 2-fluoro-6-(2-methoxy-4-propylphenoxy)pyridine by 2-fluoro-6-[2-methoxy-4-(2,2,2-trifluoroethyl)phenoxy]pyridine (0.14 mmol; 43 mg) and adding 3.5 equivalents (0.5 mmol; 500 μl) of boron tribromide, the title compound was prepared in 75% yield (0.11 mmol; 30 mg) after purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70).

Workup

  1. customafter purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-280339781c264e0380e1bb29d7b08421
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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