Sodium hydride → (3-Bromo-4-fluorobenzyl)-(2,2,3,3-tetramethylcyclopropylmethyl)ether

HRID 2232117Notes

Reaction equation

HRID 2232117 reaction equation
[CH3:1][C:2]1([CH3:9])[C:4]([CH3:6])([CH3:5])[CH:3]1[CH2:7][OH:8].[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:14]Br.[H-].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.CN(C)C=O>[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:14][O:8][CH2:7][CH:3]1[C:4]([CH3:6])([CH3:5])[C:2]1([CH3:9])[CH3:1]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5441792,2,3,3-TetramethylcyclopropanemethanolHCID 129227103-Bromo-4-fluorobenzyl Bromide

Product 1

HCID 21284399(3-Bromo-4-fluorobenzyl)-(2,2,3,3-tetramethylcyclopropylmethyl)ether

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent2×

Procedure

A solution of 20 g of 2,2,3,3-tetramethylcyclopropylmethanol and 41.9 g of 3-bromo-4-fluorobenzyl bromide in 100 ml of a 1:1 mixture of toluene/dimethylformamide is added dropwise at 0°-10° C. to 8.2 g of sodium hydride (50% dispersion in mineral oil) in 200 ml of a 1:1 mixture of toluene/dimethylformamide. When the reaction has subsided, the batch is stirred for 16 hours at room temperature and, after the dropwise addition of a saturated solution of ammonium chloride, extracted with toluene. The combined toluene extracts are washed with saturated sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The crude product is chromatographed through a column of silica gel (elution with a 5:1 mixture of hexane/ether), affording the title compound in the form of a clear oil with a refractive index of nD24 =1.5128.

Workup

  1. extractionextracted with toluene
  2. washThe combined toluene extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product is chromatographed through a column of silica gel (
  6. washelution
  7. additionwith a 5:1 mixture of hexane/ether),

Sources & evidence

ORD record
ord-147f6254145d4b4f899cea1d96c1a95d
Source dataset
uspto-grants-1988_11
Patent number
US04786654

Reaction notes

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