Boron tribromide → (R)-2((3-Bromopyridin-2-yl)oxy)propan-1-ol

HRID 1524090Notes

Reaction equation

HRID 1524090 reaction equation
C([O:8][CH2:9][C@H:10]([O:12][C:13]1[C:18]([Br:19])=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:11])C1C=CC=CC=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:19][C:18]1[C:13]([O:12][C@H:10]([CH3:11])[CH2:9][OH:8])=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 90313507(R)-2((1-(Benzyloxy)propan-2-yl)oxy)-3-bromopyridine

Product 1

HCID 90313919(R)-2((3-Bromopyridin-2-yl)oxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-2-((1-(benzyloxy)propan-2-yl)oxy)-3-bromopyridine (2.4 g, 7.5 mmol) in dry DCM (10 mL) was added BBr3 (7.5 mL, 22 mmol, 3 M in DCM) at −78 Celsius in a drop-wise manner and stirring continued for 3 h. The reaction mixture was warmed to rt and the pH adjusted to −7-8 with sat. NaHCO3 (30 mL). The mixture was extracted with DCM (2×10 mL), and the combined extracts dried over Na2SO4, filtered, concentrated to dryness. The crude product was purified by FCC to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.05-7.99 (m, 1H), 7.84-7.75 (m, 1H), 6.83-6.71 (m, 1H), 5.25-5.12 (m, 1H), 3.78 (d, J=5.1, 2H), 3.29 (s, 1H), 1.37 (d, J=6.4, 3H).

Workup

  1. extractionThe mixture was extracted with DCM (2×10 mL)
  2. dry with materialthe combined extracts dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-8298c0ba38ec440cbeba5e1967bae148
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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