Benzenesulfonyl chloride → 5-Bromo-2-butylbenzofuran

HRID 522538Notes

Reaction equation

C1(S(Cl)(=O)=O)C=CC=CC=1.C(N(CC)CC)C.[Br:18][C:19]1[CH:33]=[CH:32][C:22]([O:23][CH:24]([CH2:28][CH2:29][CH2:30][CH3:31])[C:25](O)=O)=[C:21](C=O)[CH:20]=1.CC1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:28]([C:24]1[O:23][C:22]2[CH:21]=[CH:20][C:19]([Br:18])=[CH:33][C:32]=2[CH:25]=1)[CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

25.8 ml of benzenesulfonyl chloride (0.202 mol; 1.4 equivalents) and 40 ml of toluene are placed in an equipped reactor and the mixture is stirred at 80° C. 65 ml of anhydrous triethylamine (0.47 mol) and then 45.2 g of 2-(4-bromo-2-formylphenoxy)hexanoic acid (compound VIII) (0.144 mol) dissolved in 250 ml of toluene are then added slowly at 80° C. The reaction progress is monitored by TLC (eluent: 80/20 methylcyclohexane/ethyl acetate; Rf of compound VIII=0.08; Rf of the desired compound IX=0.80).

Workup

additionare then added slowly at 80° C

Sources & evidence

ORD record: ord-aaf4388929724f84b3113c0b1d7d133a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334254B2

Reaction notes

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