tert-Butanol → 1-Bromo-3-tert-butoxy-5-fluorobenzene

HRID 658334Notes

Reaction equation

HRID 658334 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:8][C:9]1[CH:10]=[C:11]([Br:16])[CH:12]=[C:13](F)[CH:14]=1>CC(N(C)C)=O>[Br:16][C:11]1[CH:10]=[C:9]([F:8])[CH:14]=[C:13]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 568442921-Bromo-3-tert-butoxy-5-fluorobenzene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

tert-Butanol (28.2 g) is dissolved in dimethyl acetamide (200 ml). NaH (15.6 g, 60% dispersion in oil) is added over 15 minutes. The reaction mixture is stirred at room temperature for 2 hours. 3,5-difluorobromobenzene (50 g) is added drop wise over 30 minutes. The reaction mixture is stirred at room temperature until shown to be complete by HPLC. The reastion mixture is quenched by addition of water (10 ml), washed with water (1×), dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 7.00 (ddd, 1H), 6.95 (dd, 1H), 6.68 (ddd, 1H), 1.4 (s, 9H).

Workup

  1. stirringThe reaction mixture is stirred at room temperature
  2. customThe reastion mixture is quenched by addition of water (10 ml)
  3. washwashed with water (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-101f7ed79d0641a6bef670c3d6da2f2c
Source dataset
uspto-grants-2011_12
Patent number
US08076489B2

Reaction notes

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