Mesitylene → 6-Bromo-3-fluoro-2-(2-propen-1-yl)phenol

HRID 2115993Notes

Reaction equation

HRID 2115993 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[Br:12])C=C.[C:13]1(C)[CH:18]=C(C)C=C(C)[CH:14]=1>>[CH2:18]([C:10]1[C:9]([F:11])=[CH:8][CH:7]=[C:6]([Br:12])[C:5]=1[OH:4])[CH:13]=[CH2:14]

Participants

3

Reactant 2

HCID 7947MesityleneHCID 666546401-Bromo-2-allyloxy-4-fluorobenzene

Product 1

HCID 689625396-Bromo-3-fluoro-2-(2-propen-1-yl)phenolYield 95%

Procedure

Treatment of 2-(allyloxy)-1-bromo-4-fluorobenzene (12.00 g, 0.052 mol) in refluxing mesitylene generally according to the reaction procedure described for Intermediate 8 provided 11.5 g (95%) of 2-allyl-6-bromo-3-fluorophenol as a pale yellow oil. Rf=0.48 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C9H8BrFO: C, 46.78; H, 3.49. Found: C, 47.59; H, 3.47.

Workup

  1. customgenerally according to the reaction procedure

Sources & evidence

ORD record
ord-d8946032437a4924a592cac15c85b8f9
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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