Boron tribromide → HCID 58415368, compound

HRID 2075228Notes

Reaction equation

HRID 2075228 reaction equation
B(Br)(Br)Br.[I:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[O:19]C)[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C(Cl)Cl>[I:5][C:6]1[CH:7]=[C:8]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:16]=[CH:17][C:18]=1[OH:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58415249HCID 58415249, compound

Product 1

HCID 58415368HCID 58415368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (11.1 mL, 11.1 mmol, 1M in DCM) was added to a solution of 3-(3-iodo-4-methoxybenzyl)pyridine (720 mg, 2.21 mmol) in DCM (3 mL) at 0° C., and the mixture was stirred for 1 h. The mixture was quenched by the careful addition of water, the layers were separated, and the organic layer was washed with water three times. The combined organic extracts were dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 2-iodo-4-(pyridin-3-ylmethyl)phenol as a yellow oil. MS (ESI) m/z: Calculated: 311.0; Observed: 312.3 (M++1).

Workup

  1. customThe mixture was quenched by the careful addition of water
  2. customthe layers were separated
  3. washthe organic layer was washed with water three times
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-5364a949198f4dab9ecd3f4d4555dc9a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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