Hydrogen Bromide → 4'-Bromomethyl-4-decyloxybiphenyl

HRID 1955471Notes

Reaction equation

HRID 1955471 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BrH:26]>>[Br:26][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 190699634-Hydroxymethyl-4'-decyloxybiphenyl

Product 1

HCID 190699574'-Bromomethyl-4-decyloxybiphenyl

Conditions

Temperature
115 °C

Procedure

To 0.81 g (2.51 mmol) of 4-hydroxymethyl-4'-decyloxybiphenyl was added 15 ml of an aqueous solution containing 47% HBr, and then heated at 115° C. for 3 hours. After completion of the reaction, the resultant mixture was extracted with ether and washed with water, which was further washed with an aqueous solution containing saturated NaHCO3 and washed again with water. The reaction product was concentrated and, then, separated by colomun chromatography, to thereby obtain 0.92 g of 4'-bromomethyl-4-decyloxybiphenyl.

Workup

  1. customAfter completion of the reaction
  2. extractionthe resultant mixture was extracted with ether
  3. washwashed with water, which
  4. washwas further washed with an aqueous solution
  5. additioncontaining saturated NaHCO3
  6. washwashed again with water
  7. concentrationThe reaction product was concentrated
  8. customseparated by colomun chromatography

Sources & evidence

ORD record
ord-004fe70502444dc09e8ead826065f7b8
Source dataset
uspto-grants-1998_07
Patent number
US05776365

Reaction notes

Loading…