Lithium Bromide → 1-Bromo-3-(4-octylphenoxy)propan-2-ol

HRID 1821925Notes

Reaction equation

HRID 1821925 reaction equation
[CH2:1]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][CH:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br-:20].[Li+]>ClCCl>[Br:20][CH2:17][CH:15]([OH:16])[CH2:14][O:13][C:12]1[CH:18]=[CH:19][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 107248((p-Octylphenoxy)methyl)oxirane

Product 1

HCID 116171121-Bromo-3-(4-octylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.17 g (4.46 mmol) 2-(4-octyl-phenoxymethyl)oxirane are dissolved in 10 ml absolute dichloromethane and mixed with 1.34 g (22.3 mmol) silica gel and with 1.16 g (13.4 mmol) lithium bromide. The suspension is concentrated almost to dryness on the rotary evaporator and allowed to stand at room temperature for 3 hours. The reaction batch is mixed with dichloromethane, filtrated on cotton wool and concentrated on the rotary evaporator. Taking up the suspension in diethyl ether, washing with water, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator yield the product as a yellowish oil.

Workup

  1. concentrationThe suspension is concentrated almost to dryness on the rotary evaporator
  2. additionThe reaction batch is mixed with dichloromethane
  3. filtrationfiltrated on cotton wool
  4. concentrationconcentrated on the rotary evaporator
  5. washwashing with water
  6. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator

Sources & evidence

ORD record
ord-fae531810d3b4b33b125ae8da3994c67
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…