Anisole → 4-Bromoanisole

HRID 1918393Notes

Reaction equation

HRID 1918393 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]1([O:15][CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:8][C:12]1[CH:13]=[CH:14][C:9]([O:15][CH3:16])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 67184N-bromobutanimide2×

Product 1

HCID 77304-BromoanisoleYield 98%

Reagents, catalysts & solvents 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-Catalyst

Procedure

Bromination using NBS has been found to be applicable for use with a wide range of aromatic starting materials or substrates, as is summarized in Table 1. For example, anisole can be brominated by use of 1 equivalent of NBS in the presence of 5 mol % of ZrCl4 at −78° C. to afford p-bromoanisole in 98% yield as sole product (Table 1, Entry 1). However, in the absence of ZrCl4 the halogenation does not proceed, even at room temperature (Table 1, Entry 1).

Sources & evidence

ORD record
ord-934cb820085e430590ab2c02b2e97f1d
Source dataset
uspto-grants-2013_12
Patent number
US08618320B2

Reaction notes

Loading…