11-Bromoundecanoic acid → Undecanoyl chloride, 11-bromo-

HRID 265997Notes

Reaction equation

HRID 265997 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.O=S(Cl)[Cl:17]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:17])=[O:14]

Participants

4

Reactant 2

HCID 1781211-Bromoundecanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 85202Undecanoyl chloride, 11-bromo-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification:

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-788d43050e674b10870d83acc19291d6
Source dataset
uspto-grants-1997_07
Patent number
US05650101

Reaction notes

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