Potassium Carbonate → HCID 22601752, compound

HRID 1987713Notes

Reaction equation

HRID 1987713 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+]>>[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

4

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 699793-Bromobenzyl bromide

Product 1

HCID 22601752HCID 22601752, compound

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 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. concentrationconcentrated in vacuo
  2. custompartitioned between Et2O (300 mL) and water (300 mL)
  3. washThe organic phase was washed with aqueous NaOH (1 M, 300 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72a9989de7bd4527992734baac9aab39
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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