Water → 1-Bromo-2-(2-bromo-6-fluoro-benzyloxy)-4-fluoro-benzene

HRID 1670598Notes

Reaction equation

HRID 1670598 reaction equation
[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)CBr.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[OH:19].[C:20](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[O:19][CH2:20][C:5]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenolHCID 673345941-Bromo-3-fluorobenzyl bromide

Product 1

HCID 673347191-Bromo-2-(2-bromo-6-fluoro-benzyloxy)-4-fluoro-benzeneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-3-fluorobenzyl bromide (1.75 kg, 6.52 mol) and 2-bromo-5-fluorophenol (730 mL, 16.56 mol, 1.01 eq) in N,N-dimethylformamide (14 L) at 0° C. add potassium carbonate (1.36 kg, 9.80 mol) in one portion and stir the resulting slurry cold for one hour and then at room temperature overnight. Transfer the reaction mixture to a 50 liter flask, add water (14 L) drop wise over 30 min and ice periodically to control the exotherm of the crystallization. Stir at room temperature for one hour, collect off-white solids by filtration, wash with water, and dry overnight at 50° C. to obtain the title compound (2.22 kg, 90%). 1H NMR (CDCl3) δ 7.51 (m, 2H), 7.30 (m, 1H), 7.14 (t, 1H), 6.89 (dd, 1H), 6.67 (m, 1H), 5.26 (d, 2H).

Workup

  1. customat room temperature
  2. customovernight
  3. customthe exotherm of the crystallization
  4. stirringStir at room temperature for one hour
  5. customcollect off-white solids
  6. filtrationby filtration
  7. washwash with water
  8. customdry overnight at 50° C.

Sources & evidence

ORD record
ord-9338fff8ae4347f58776b7ff9b0a5d1d
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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