Thionyl bromide → 4-(3-Chloropropoxy)-benzyl bromide

HRID 722075Notes

Reaction equation

HRID 722075 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]O)=[CH:8][CH:7]=1.S(Br)([Br:16])=O>O1CCOCC1.C(OCC)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][Br:16])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 68176Thionyl bromideHCID 228974964-(3-Chloropropoxy)benzyl alcohol

Product 1

HCID 218822764-(3-Chloropropoxy)-benzyl bromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution consisting of 4-(3-chloropropoxy)-benzyl alcohol No. 162 (10.6 g, 52.8 mmol) in dioxane (0.125 l) was cooled to 0° C. and treated with a dropwise addition of thionyl bromide (12.0 g, 58.0 mmol). After 10 minutes the reaction was complete. The dioxane was diluted with ethyl ether and washed with water, brine, and then dried over MgSO4. The material was concentrated down to yield 15 g of an oil: 1H NMR (DMSO) 7.36 (d, 2 H, J=8.8 Hz), 6.92 (d, 2 H, J=8.6 Hz), 4.68 (s, 2 H), 4.08 (t, 2 H, J=5.9 Hz), 3.77 (t, 2 H, J=6.4 Hz); MS (FAB) 266 (M+H+).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationThe material was concentrated down

Sources & evidence

ORD record
ord-dd4bd2aff566470d9c53af0a38dca504
Source dataset
uspto-grants-2006_11
Patent number
US07138392B2

Reaction notes

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