Benzenesulfonyl chloride → 5-Bromo-2-butylbenzofuran

HRID 541095Notes

Reaction equation

HRID 541095 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

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 220578262-(4-Bromo-2-formylphenoxy)hexanoic acid3×HCID 66985183Ethyl acetate methylcyclohexane

Product 1

HCID 569260235-Bromo-2-butylbenzofuran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

25.8 ml of benzenesulfonyl chloride (0.202 mol; 1.4 equivalent) 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 XI) (0.144 mol) in solution in 250 ml of toluene are slowly added at 80° C. The progress of the reaction is monitored by TLC (eluent: methylcyclohexane/ethyl acetate: 80/20; Rf of compound XI=0.08; Rf of the desired compound XII=0.80).

Sources & evidence

ORD record
ord-b2e33026cbe942739a950d8dc089d96e
Source dataset
uspto-grants-2014_10
Patent number
US08871956B2

Reaction notes

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