Sodium Iodide → HCID 22601752, compound

HRID 2308349Notes

Reaction equation

HRID 2308349 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13]Br.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(C)=O>[Br:9][C:10]1[CH:11]=[C:12]([CH2:13][O:8][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 699793-Bromobenzyl bromide

Product 1

HCID 22601752HCID 22601752, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-bromophenol (13.8 g, 80 mmol), 3-bromobenzyl bromide (10 g, 40 mmol), K2CO3 (16.6 g. 120 mmol) and NaI (300 mg, 2 mmol) in acetone (100 mL) was heated to reflux for 12 hours. The reaction mixture was cooled to rt, concentrated in vacuo and partitioned between Et2O (300 mL) and water (300 mL). The organic phase was washed with aqueous NaOH (1 M, 300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 3-[(m-bromophenyl)methoxy]bromobenzene as a clear oil. MS (APCI) m/z 339 (M+−3, 50%), 341 (M+−1, 100%), 343 (M++3, 50%), 13C NMR (50 MHz, CDCl3); δ 68.9, 113.4, 117.9, 122.5, 122.6, 124.1, 125.6, 129.9, 130.0, 130.4, 130.9, 138.4, 158.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. concentrationconcentrated in vacuo
  4. custompartitioned between Et2O (300 mL) and water (300 mL)
  5. washThe organic phase was washed with aqueous NaOH (1 M, 300 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64f111930d634f39ab5ba35b6ea8f2d9
Source dataset
uspto-grants-2004_12
Patent number
US06835753B2

Reaction notes

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