Hydrochloric Acid → HCID 54536536, compound

HRID 1590400Notes

Reaction equation

HRID 1590400 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([Br:14])[Br:13])=[CH:7][CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl>[Br:13][C:12]([Br:14])=[CH:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][OH:3])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11256090Benzoic acid, 4-(2,2-dibromoethenyl)-, ethyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 54536536HCID 54536536, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above ester (3.32 g) in dichloromethane (10 ml) at 0.20° under nitrogen was treated with diisobutyl aluminiumhydride (21 ml). After 1 hour at 0° C. dilute hydrochloric acid was added and the mixture worked up in the normal manner to give 4-(2,2-dibromoethenyl)benzyl alcohol (3.18 g). NMR 1H 7.50(2H,d), 7.41(1H,s), 7.20(2H,d), 4.33(2H,s), 3.65(1H,s).

Sources & evidence

ORD record
ord-ebbb8928561e49439ec7d76431714d92
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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