Dimethyl Sulfoxide → HCID 19769964, compound

HRID 1590401Notes

Reaction equation

HRID 1590401 reaction equation
[Br:1][C:2]([Br:12])=[CH:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[Br:1][C:2]([Br:12])=[CH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 54536536HCID 54536536, compound

Product 1

HCID 19769964HCID 19769964, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above alcohol (3.18 g) was oxidised using the conditions of Swern oxalyl chloride, 0.96 ml, dimethyl sulphoxide, 1.56 ml; triethylamine, 6.9 ml) in dichloromethane to give 4-(2,2-dibromoethenyl)benzaldehyde (2.04 g). NMR 1H 10.94 (1H,s), 7.86(2H,d), 7.61(2H,d), 7.45(1H,s).

Sources & evidence

ORD record
ord-4972058eb503480b9a5f4f5138c7c602
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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