Triethylamine → HCID 131720044, compound

HRID 1683434Notes

Reaction equation

HRID 1683434 reaction equation
[Br:1][CH2:2][C:3]([CH2:19][O:20][C:21]([F:31])([F:30])[C:22]([F:29])([F:28])[CH2:23][C:24]([F:27])([F:26])[F:25])([CH2:6][O:7][C:8]([F:18])([F:17])[C:9]([F:16])([F:15])[CH2:10][C:11]([F:14])([F:13])[F:12])[CH2:4][OH:5].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>C(Cl)Cl.CS(Cl)(=O)=O>[S:33]([O:5][CH2:4][C:3]([CH2:6][O:7][C:8]([F:17])([F:18])[C:9]([F:15])([F:16])[CH2:10][C:11]([F:14])([F:13])[F:12])([CH2:19][O:20][C:21]([F:30])([F:31])[C:22]([F:28])([F:29])[CH2:23][C:24]([F:25])([F:26])[F:27])[CH2:2][Br:1])(=[O:35])(=[O:34])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86750952HCID 86750952, compound

Product 1

HCID 131720044HCID 131720044, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 31297Methanesulfonyl chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to that described above, 3-bromo-2,2-bis-(heptafluorobutoxymethyl)-1-propanol (250.0 g, 0.44 mole) was reacted with methanesulfonyl chloride (58.45 g, 0.51 mole) and triethylamine (52.62 g, 0.52 mole) in methylene chloride (400+200 ml). Additional methanesulfonyl chloride (2.96 g, 0.03 mole) was added to bring the reaction to completion. Washing and removal of the solvent gave 268.4 g (95.2%) of 3-bromo-2,2-bis(heptafluorobutoxymethyl)-1-propanol mesylate (4), a yellow oil: IR 2940, 1350, 1223, 1176, and 1120 cm-1 ; 1H NMR (CDCl3) 3.02 (s, 3H), 3.49 (s, 2H), 3.68 (s, 4H), 3.97 (t, J=13.3 Hz, 4H), and 4.24 (s, 2H); 13C NMR (CDCl3) 31.66, 36.64, 44.60, 67.81 (t, J=26.44), 68.36, and 70.30. Anal. Calcd for C14H15BrF14O5S: C, 26.22; H, 2.36; Br, 12.46, F, 41.48. Found: C, 25.95; H, 2.33; Br, 12.88.

Workup

  1. customthe reaction to completion
  2. washWashing
  3. customremoval of the solvent

Sources & evidence

ORD record
ord-24eef4e1aa474d38b02b468a9e18a9b1
Source dataset
uspto-grants-1997_06
Patent number
US05637772

Reaction notes

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