ChemicalBook CAS DataBase List (4-BROMO-BENZYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER

(4-BROMO-BENZYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER synthesis

3synthesis methods

Product Name:(4-BROMO-BENZYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER
CAS Number:260809-26-5
Molecular formula:C13H18BrNO2
Molecular Weight:300.19

68819-84-1 Synthesis

68819-84-1
115 suppliers
$11.00/250mg

74-88-4
346 suppliers
$15.00/10g

(4-BROMO-BENZYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER

260809-26-5
28 suppliers
$98.00/50mg

Yield:-

Reaction Conditions:

with silver(l) oxide in N,N-dimethyl-formamide at 50; for 18 h;

Steps:

V.V-2.b tert-Butyl-4-bromobenzyl(methyl)carbamate
In a 60-mL vial, tert-butyl-4-bromobenzylcarbamate (1.25 g, 4.37 mmol) was dissolved in DMF (12 mL).
To this solution was added Ag₂O (4.0 g, 17 mmol) followed by the addition of CH₃I (0.68 mL, 11 mmol).
The mixture was stirred at 50° C. for 18 hours.
The reaction mixture was filtered through a bed of celite and the celite was washed with methanol (2*20 mL) and dichloromethane (2*20 mL).
The filtrate was concentrated to remove most of the DMF.
The residue was treated with water (50 mL) and a white emulsion formed.
This mixture was extracted with ethyl acetate (4*25 mL), dried over Na₂SO₄, and the solvent was evaporated to yield tert-butyl-4-bromobenzyl(methyl)carbamate as a yellow oil. ¹H NMR (300 MHz, DMSO-d₆) δ 7.53 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 4.32 (s, 2H), 2.74 (s, 3H), 1.38 (s, 9H).

References:

Vertex Pharmaceuticals Incorporated;Van Goor, Fredrick F.;Burton, William Lawrence US2015/231142, 2015, A1 Location in patent:Paragraph 1376

24424-99-5 Synthesis