1,4-Dibromobutane → HCID 43519349, compound

HRID 1524133Notes

Reaction equation

HRID 1524133 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9].Br[CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1([C:12]#[N:13])[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 43519215HCID 43519215, compound

Product 1

HCID 43519349HCID 43519349, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(2-bromophenylsulfonyl)acetonitrile (4.4 g, 17 mmol), tetrabutylammonium bromide (0.82 g, 2.6 mmol), 1,4-dibromobutane (3.85 g, 17.8 mmol) and NaOH (14 mL, 5 N) in DCM (30 mL) was stirred at rt for 5 h, before diluting with DCM (200 mL), washing with water (2×80 mL) and brine (60 mL), drying over Na2SO4, filtering, and concentrating to dryness. The residue was treated with IPA (20 mL) and sonicated before isolating the title compound (2.2 g) via vacuum filtration. The filtrate was concentrated to dryness and the resultant residue subjected to FCC to give additional title compound. MS (ESI): mass calcd. for C12H12BrFN3O2S, 312.98; m/z found, 314.0 [M+H]+. 1HNMR (300 MHz, CDCl3) δ 8.28 (dd, J=7.5, 1.5, 1H), 7.85 (dd, J=7.5, 1.5, 1H), 7.62-7.51 (m, 2H), 2.80-2.68 (m, 2H), 2.34-2.22 (m, 2H), 2.02-1.81 (m, 4H).

Workup

  1. washwashing with water (2×80 mL) and brine (60 mL)
  2. dry with materialdrying over Na2SO4
  3. filtrationfiltering
  4. concentrationconcentrating to dryness
  5. additionThe residue was treated with IPA (20 mL)
  6. customsonicated

Sources & evidence

ORD record
ord-ce7eb299faee43b2b0b235cd53a64014
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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