Hydrogen Bromide → 1-(Bromomethyl)-2-phenylbenzene

HRID 67810

Reaction equation

HRID 67810 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]([CH2:7]O)=[CH:3][CH:4]=[CH:5][CH:6]=1.S(=O)(=O)(O)O.[BrH:20]>>[Br:20][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 76229(1,1'-Biphenyl)-2-methanol

Product 1

HCID 2633651-(Bromomethyl)-2-phenylbenzene

Procedure

A stirred solution of 58.9 g (0.319 mole) of 2-biphenylmethanol and 6 ml of concentrated sulfuric acid in 67 ml of aqueous 48% hydrobromic acid was heated under reflux for 5 hours. The reaction mixture was cooled to ambient temperature, poured into ice-water, and the resulting mixture extracted with three portions of 100 ml each of diethyl ether. The combined extracts were washed with 50 ml of a saturated aqueous solution of sodium bicarbonate, then with 50 ml of water. The organic layer was dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give 76.8 g of 2-(bromomethyl)biphenyl as a residual oil. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionthe resulting mixture extracted with three portions of 100 ml each of diethyl ether
  3. washThe combined extracts were washed with 50 ml of a saturated aqueous solution of sodium bicarbonate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d6c8902f3454a819eb08efe3074142c
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Linked notes

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