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

HRID 1074496Notes

Reaction equation

HRID 1074496 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 was 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 was 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 was added. The mixture was then warmed to room temperature and stirred 30 minutes longer. It was quenched by addition to 6 liters of ice water. The quenched mixture was extracted six times with 500 ml. of ether. The combined extract was 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 was quenched by addition to 6 liters of ice water
  4. extractionThe quenched mixture was extracted six times with 500 ml
  5. extractionThe combined extract
  6. washwas 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-d5d9f3c8eb5345b191c72007d4e0e862
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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