Dimethylformamide → Undecanoyl chloride, 11-bromo-

HRID 2364896Notes

Reaction equation

HRID 2364896 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.CN(C=O)C.S(Cl)([Cl:22])=O>ClCCl>[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:22])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1781211-Bromoundecanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 85202Undecanoyl chloride, 11-bromo-Yield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
39 °C

Procedure

20.0 g of 11-bromoundecanoic acid (0.0754 mol) are placed in 20 ml dichloromethane in the presence of 0.28 g DMF (0.05 eq). The reaction mixture is heated to reflux and 10.68 g of thionyl chloride (0.0905 mol) are added drop wise over a period of 1 h 40 min at 39° C. After 3 h at 39° C. the reaction mixture is cooled down to r.t. and evaporated to dryness, yielding to 7.9 g of the expected compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-ee60086a584246278668948e4639fdeb
Source dataset
uspto-grants-2014_04
Patent number
US08697101B2

Reaction notes

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