Dimethyl Sulfate → 1-Bromo-3,5-di-tert-butyl-2-methoxybenzene

HRID 2261526Notes

Reaction equation

HRID 2261526 reaction equation
[CH3:1][O:2][CH2:3]OCOC.[C:8]([C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])C=[C:14]([Br:22])[CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C(Cl)OC.COS(OC)(=O)=O.C(C1C=C(C(C)(C)C)C=CC=1O)(C)(C)C>>[CH3:1][O:2][C:3]1[C:14]([Br:22])=[CH:13][C:12]([C:8]([CH3:10])([CH3:9])[CH3:11])=[CH:17][C:16]=1[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 73112,4-Di-tert-butylphenolHCID 7864Chloromethyl Methyl EtherHCID 687815021-Methoxymethylether 2,4-di-t-butyl-6-bromobenzene

Product 1

HCID 154059401-Bromo-3,5-di-tert-butyl-2-methoxybenzeneYield 92%

Procedure

A procedure analogous the synthesis of 1-methoxymethylether-2,4-di-t-butyl-6-bromobenzene was employed. The MOMCl was replaced with Me2SO4 as alkylating agent. Starting from 20 g of 2,4-di-t-butyl-phenol, 26.8 g (92% yield over two steps) of 1-methoxy-2,4-di-t-butyl-6-bromobenzene were obtained. 1H NMR (300 MHz, CDCl3) δ: 1.30 (s, 9H, C(CH3)3), 1.41 (s, 9H, C(CH3)3), 3.92 (s, 3H, OCH3), 7.29 (d, 2H, aryl-H, 4J=2.3 Hz), 7.42 (d, 2H, aryl-H, 4J=2.3 Hz). 13C NMR (75 MHz, CDCl3) δ: 31.1 (C(CH3)3), 31.6 (C(CH3)3), 34.8 (C(CH3)3), 35.9 (C(CH3)3), 61.5 (OCH3), 117.8, 123.8, 129.0, 144.2, 147.4, 154.3 (aryl). GC-MS: M+=298.

Sources & evidence

ORD record
ord-24c2048c80f040cc854dcabd2ef3e6d8
Source dataset
uspto-grants-2010_12
Patent number
US07847099B2

Reaction notes

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