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

HRID 366306

Reaction equation

HRID 366306 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: 1H NMR (CDCl3) δ 1.26 (bs, (CH2)5, 10 H), 1.34 (m, CH2CH2CH2Br, 2 H), 1.67 (m, CH2CH2COCl, 2 H), 1.81 (m, CH2CH2Br, 2 H), 2.85 (t, CH2COCl, J=7.2 Hz, 2 H), 3.36 (t, CH2Br, J=6.8 Hz, 2 H); 13C NMR (CDCl3) δ 24.89 (CH2CH2COCl), 27.95 (CH2CH2CH2Br), 28.21, 28.52, 28.84, 29.02, and 29.12 ((CH2)5), 32.64 (CH2CH2Br), 33.80 (CH2Br), 46.92 (CH2COCl), 173.47 (COCl).

Workup

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

Sources & evidence

ORD record
ord-c8447bc91b0f4446b1ce54542f7f42e1
Source dataset
uspto-grants-2000_10
Patent number
US06130209

Linked notes

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