Dimethylformamide → 4-(3-Chloropropoxy)benzenesulfonyl chloride

HRID 722458Notes

Reaction equation

HRID 722458 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:12][S:13](O)(=[O:15])=[O:14].C(Cl)(=O)C(Cl)=O.CN(C=O)C>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chlorideHCID 76917(3-Chloropropoxy)benzene

Product 1

HCID 218847304-(3-Chloropropoxy)benzenesulfonyl chlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 52.75 g (0.265 mol) of (3-chloro-propoxy)-benzene in 100 ml of CH2Cl2, a solution of 19.4 ml (0.292 mol) of chlorosulfonic acid in 100 ml of CH2Cl2 is added dropwise at 0–5° C. under N2 atmosphere. The mixture is allowed to warm to ambient temperature and stirred for 2 hours. To the mixture, 29.6 ml (0.345 mol) of oxalyl chloride and 4 ml (0.052 mol) of DMF are added dropwise at r.t. and the mixture is stirred for 18 h at r.t. The reaction mixture is poured into ice-water, extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated under reduced pressure to give 58.5 g of 4-(3-chloropropoxy) benzenesulfonyl chloride; NMR(CDCl3): 2.26–2.36 (m, 2H), 3.76 (t, 2H, J=6.04 Hz), 4.24 (t, 2H, J=6.04 Hz), 7.06 (d, 2H, J=9.08 Hz), 7.98 (d, 2H, J=9.08 Hz).

Workup

  1. stirringthe mixture is stirred for 18 h at r.t
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts are dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f850a5d363df4056be041a7ee7b8cb3f
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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