Hydrogen Bromide → 4-(Bromomethyl)-4'-pentyl-1,1'-biphenyl

HRID 370697Notes

Reaction equation

HRID 370697 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BrH:20].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:20][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 13531318HCID 13531318, compound

Product 1

HCID 202750004-(Bromomethyl)-4'-pentyl-1,1'-biphenylYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9.4 g of 4-(hydroxymethyl)-4'-pentylbiphenyl in 150 ml of methylene chloride was placed at 0° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 3.4 ml of a 62% aqueous hydrogen bromide solution. The mixture was subsequently stirred at room temperature for a further 15 hours, then poured into 50 ml of 5% sodium hydrogen carbonate solution and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (10.8 g) on silica gel with 5% ethyl acetate/petroleum as the eluant gave 7.5 g (64%) of 4-(bromomethyl)-4'-pentylbiphenyl as a colourless oil.

Workup

  1. extractionextracted three times with 100 ml of methylene chloride each time
  2. washThe organic phases were washed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a2ce720a8dc437eaa4b48bc9d33122e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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