Hydrogen Bromide → 5-(3-Bromopropyl)-2-(2-fluorophenyl)pyridine

HRID 1896693Notes

Reaction equation

HRID 1896693 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16]O)=[CH:10][CH:9]=1.[BrH:18]>>[Br:18][CH2:16][CH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 691058943-[6-(2-Fluorophenyl)pyridin-3-yl]propan-1-ol

Product 1

HCID 691059795-(3-Bromopropyl)-2-(2-fluorophenyl)pyridine

Procedure

230 mg (0.99 mmol) of 3-(6-(2-fluorophenyl)pyridin-3-yl)propan-1-ol were stirred in 10 ml of hydrobromic acid (33% in acetic acid) at 60° C. for 6 h. After concentrating, a sodium hydrogencarbonate solution was added, the resulting mixture was extracted with ethyl acetate, and the organic phase was separated and concentrated. Yield: 707 mg (71%).

Workup

  1. concentrationAfter concentrating
  2. additiona sodium hydrogencarbonate solution was added
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. customthe organic phase was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4147e10a44414370a71c54a870ac4a8b
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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