Bis(Chloromethyl) Ether → 1-(Chloromethyl)-2-fluoro-3,4-dimethoxybenzene

HRID 1283899Notes

Reaction equation

HRID 1283899 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.FC1C=CC=C(OC)C=1OC.[Cl:25]COCCl>C(O)(=O)C>[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH2:4][Cl:25]

Participants

5

Reactant 3

HCID 10967Bis(Chloromethyl) EtherHCID 6035882-Fluoro-3,4-dimethoxybenzaldehydeHCID 27589791-Fluoro-2,3-dimethoxybenzene

Product 1

HCID 2374111-(Chloromethyl)-2-fluoro-3,4-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 2-fluoroveratraldehyde used as indicated above is prepared as follows: 3-fluoroveratrole is reacted with monochloromethyl ether in glacial acetic acid to give 2-fluoro-3,4-dimethoxybenzyl chloride which is treated with hexamethylenetetramine in chloroform followed by refluxing in 50% acetic acid to yield the 2-fluoroveratraldehyde.

Workup

  1. customabove is prepared

Sources & evidence

ORD record
ord-698568d1285144f38373b489a08d7a01
Source dataset
uspto-grants-1976_08
Patent number
US03976695

Reaction notes

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