Benzyl Bromide → 2-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

HRID 444356Notes

Reaction equation

HRID 444356 reaction equation
[H-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:18])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:6][C:5]=1[OH:19].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([O:19][C:5]1[CH:6]=[C:7]([C:10]([CH3:18])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])[CH:8]=[CH:9][C:4]=1[Br:3])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 82127Potassium hydrideHCID 127881872-Bromo-5-(2-methyloctan-2-YL)phenol

Product 1

HCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a -18° C. slurry of 23.0 g. (0.575 mole) of potassium hydride in 400 ml. of N,N-dimethylformamide is added over a 45 minute period a solution of 150 g. (0.5 mole) of 2-(4-bromo-3-hydroxyphenyl)-2-methyloctane in 400 ml. of N,N-dimethylformamide (reaction temperature ≤-15° C.). The reaction mixture is stirred 15 minutes longer after which a solution of 98.3 g. (0.575 mole) of benzyl bromide in 200 ml. of N,N-dimethylformamide is added. The mixture is then warmed to room temperature and stirred 30 minutes longer. It is quenched by addition to 6 liters of ice water. The quenched mixture is extracted six times with 500 ml. of ether. The combined extract is washed twice with one liter portions of water and once with one liter of saturated sodium chloride, dried over magnesium sulfate and evaporated to a quantitative yield of the title product.

Workup

  1. customTo a -18° C.
  2. stirringstirred 30 minutes longer
  3. customIt is quenched by addition to 6 liters of ice water
  4. extractionThe quenched mixture is extracted six times with 500 ml
  5. extractionThe combined extract
  6. washis washed twice with one liter portions of water and once with one liter of saturated sodium chloride
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-b7098a052a3c482281fcc53c0acd1bfa
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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