Benzene → Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonyl chloride

HRID 1746356Notes

Reaction equation

HRID 1746356 reaction equation
S(Cl)([Cl:3])=O.[C:5]12[CH2:12][CH:11]([C:13]([OH:15])=O)[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2.C1C=CC=CC=1>ClCCl>[C:5]12[CH2:12][CH:11]([C:13]([Cl:3])=[O:15])[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 3023241-Benzocyclobutenecarboxylic acid

Product 1

HCID 22956883Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.5 ml) was added to a solution of bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid [14381-41-0] (0.001 mol) in dichloromethane. The reaction mixture was refluxed for 1 hour. Then stirred overnight at room temperature. The solvents were co-evaporated 2 times with benzene to obtain bicyclo[4.2.0]octa-1,3,5-triene-7-carbonyl chloride [1473-47-8] which was dissolved in DIPE. The obtained solution was added dropwise to a cooled mixture (0° C.) of N-allyl-2-adamantanamine [24161-63-5] and sodium carbonate in DIPE. The reaction mixture was stirred for 30 minutes on ice and then for 2 hours at room temperature. The mixture was poured out into water and extracted with dichloromethane. The organic layer was filtered through Extrelut™ and the filtrate was evaporated. The residue was purified by flash column chromatography on TRIKONEX FlashTube™ (eluent: CH2Cl2/EtOAc 90/10). The product fractions were collected and the solvents were evaporated, yielding 0.13 g of intermediate 1.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour

Sources & evidence

ORD record
ord-b3393a9161474e7db1dc37be7fdbf011
Source dataset
uspto-grants-2015_10
Patent number
US09150512B2

Reaction notes

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