Water → 4-(3-Bromopropyl)phenol

HRID 2227105Notes

Reaction equation

HRID 2227105 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.[Br:12]C(Br)(Br)Br.O>ClCCl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11205Carbon tetrabromideHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 148170364-(3-Bromopropyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-hydroxyphenyl)-1-propanol 3A (4.0 g) and tripohenylphosphine (7.96 g) in anhydrous dichloromethane (77 mL), cooled to 0° C., is added, dropwise, a solution of tetrabromomethane (9.59 g) in anhydrous dichloromethane (15.4 mL). The reaction mixture gradually warmed to room temperature and allowed to stir overnight. The solution is then poured into water and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo.

Workup

  1. additionis added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-ddc232abfd544438b4acbac4d5921aaa
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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