2-Bromobenzenesulfonyl chloride → HCID 90314534, compound

HRID 1523761Notes

Reaction equation

HRID 1523761 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].Cl.[F:13][C:14]1([F:19])[CH2:18][CH2:17][NH:16][CH2:15]1>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:16]1[CH2:17][CH2:18][C:14]([F:19])([F:13])[CH2:15]1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 5204032-Bromobenzenesulfonyl chlorideHCID 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 90314534HCID 90314534, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromobenzene-1-sulfonyl chloride (0.300 g, 1.17 mmol) and 3,3-difluoropyrrolidine hydrochloride (0.169 g, 1.17 mmol) in pyridine (5 mL) was stirred for 16 hours at 60° Celsius. The reaction was then cooled to rt, diluted with EtOAc (25 mL), washed with 1 N HCl (2×25 mL), and brine (50 mL). The organic layer was isolated, dried over MgSO4, filtered and concentrated to dryness to yield the title compound (0.335 g, 86%), The product was used without further purification. 1H NMR (500 MHz, CDCl3) δ 8.13-8.09 (m, 1H), 7.80-7.76 (m, 1H), 7.50-7.41 (m, 2H), 3.74 (t, J=12.8, 2H), 3.67 (t, J=7.2, 2H), 2.44-2.35 (m, 2H).

Workup

  1. washwashed with 1 N HCl (2×25 mL), and brine (50 mL)
  2. customThe organic layer was isolated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a3d81a64f122430ba10a1998e5632597
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…