N-bromobutanimide → 1-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

HRID 1602400Notes

Reaction equation

HRID 1602400 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[C:10]=1[CH3:11].FC1C(C)=C[C:16]2[O:20]C=CC=2C=1.BrN1[C:28](=[O:29])CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH3:28][O:29][CH:7]([O:20][CH3:16])[CH2:8][O:9][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:10]([CH3:11])[CH:6]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 196116355-Fluoro-4-methylbenzofuranHCID 196116815-Fluoro-6-methylbenzofuran

Product 1

HCID 196116591-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-fluoro-4-methylbenzofuran and 5-fluoro-6-methylbenzofuran (14.95 g), N-bromosuccinimide (16.57 g), benzoyl peroxide (0.32 g) and carbon tetrachloride (375 ml) was heated under reflux under the illumination of an 80 W flood lamp for 20 h. The mixture was cooled, and filtered and the filtrate evaporated to dryness to give the crude product as an oil (24.0 g). This material was combined with a similar crude product (6.94 g) from an identical reaction run on a smaller scale and purified by chromatography on silica (900 g) using an ether hexane mixture (1:30) as eluant to give the title compound (13.5 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under the illumination of an 80 W flood lamp for 20 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. customto give the crude product as an oil (24.0 g)
  7. custompurified by chromatography on silica (900 g)

Sources & evidence

ORD record
ord-75006e1a592b49ff9fbbd6f61b228e6b
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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