Phosphorus tribromide → 2,3-Dimethoxybenzyl bromide

HRID 2296364Notes

Reaction equation

HRID 2296364 reaction equation
C(O)(=O)C.C(C1C=CC=C(O)C=1O)CCCCCCCCCCCCCCCCCC.[CH3:32][O:33][C:34]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=O.[BH4-].[Na+].P(Br)(Br)[Br:47]>>[CH3:32][O:33][C:34]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36][Br:47]

Participants

5

Reactant 4

HCID 24614Phosphorus tribromideHCID 665812,3-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 70501056HCID 70501056, compound

Product 1

HCID 107281972,3-Dimethoxybenzyl bromide

Procedure

The nonadecylcatechol acetate (NDC-AC) used in the tests was prepared as follows: 2, 3 dimethoxybenzaldehyde was reduced in the presence of sodium borohydride and the reduction product reacted with phosphorus tribromide to form 2, 3 dimethoxybenzylbromide. The benzylbromide reaction product was refluxed with triphenyl phosphine in xylene to form 2, 3 dimethoxybenzyl-triphenyl phosphonium bromide which was then reacted with octadecanal in the presence of butyl lithium to form 2, 3 dimethoxy-nonadecenylbenzene. Subsequent steps of reduction and reaction with boron tribromide produced 3-nonadecylcatechol which was purified by chromatography. The catechol was acetylated with acetic anhydride in pyridine to form the acetate (NDC-AC).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-c1b8b69eb9b54e6690c16c7f5d273ec9
Source dataset
uspto-grants-1984_01
Patent number
US04428965

Reaction notes

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