4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-(3-bromophenyl)butyl ester

HRID 30564Notes

Reaction equation

HRID 30564 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 218954894-(3-Bromophenyl)butan-1-ol

Product 1

HCID 57435871Toluene-4-sulfonic acid 4-(3-bromophenyl)butyl esterYield 133.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of 4-(3-bromophenyl)butan-1-ol (1.08 g, 4.7 mmol) and p-toluenesulfonyl chloride (1.2 g, 6.3 mmol) in THF was treated slowly with triethyl amine (1.8 mL, 12.3 mmol), stirred at room temperature for 4 hours, poured into cold saturated aqueous NH4Cl and extracted with ether. The organic extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue on silica gel (ISCO) using (hexanes/EtOAC 9.5/0.5) as the eluting solvent afforded toluene-4-sulfonic acid 4-(3-bromophenyl)-butyl ester as a colorless oil (2.4 g, 76% yield). m/e (M+NH4)+ 400.1. 1H NMR (400 MHZ, DMSO-d6) δ ppm, 1.4-1.6 (m, 4 H), 2.4 (s, 3 H), 2.4-2.5 (m, 2 H), 4.0 (t, J=6.0 Hz, 2 H), 7.2 (t, J=7.8 Hz, 1 H), 7.3-7.3 (m, 1 H), 7.3-7.3 (m, J=8.0, 1.0 Hz, 1 H), 7.4-7.5 (m, J=8.6 Hz, 2 H), 7.7-7.8 (m, 2 H).

Workup

  1. extractionextracted with ether
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the resultant residue on silica gel (ISCO)

Sources & evidence

ORD record
ord-17ff9177d67b4daea96f547a09703f58
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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