ChemicalBook CAS DataBase List 5-BROMOPENTANOIC ACID, T-BUTYL ESTER

5-BROMOPENTANOIC ACID, T-BUTYL ESTER synthesis

6synthesis methods

Product Name:5-BROMOPENTANOIC ACID, T-BUTYL ESTER
CAS Number:88987-42-2
Molecular formula:C9H17BrO2
Molecular Weight:237.13

4509-90-4 Synthesis

4509-90-4
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$15.00/1g

75-65-0 Synthesis

75-65-0
753 suppliers
$10.00/10ml

88987-42-2
78 suppliers
$9.00/100mg

Yield: 3.02 g

Reaction Conditions:

with oxalyl dichloride in dichloromethane at 0 - 20;

Steps:

1.ED.3 Step 3: tert-Butyl 5-bromopentanoate
To a solution of 5-bromovaleric acid (2.5 g, 14.0 mmol) in dichloromethane (10 mL) was added oxalyl chloride (1.15 mL, 13.2 mmol) and the reaction mixture stirred at room temperature for 4 hours. The solvent and excess oxalyl chloride were removed under vacuum. The crude acid chloride was dissolved in dichloromethane (10 mL) and cooled to 0°C. Then fert-butanol (10 mL) was added and the reaction mixture stirred at room temperature overnight. The solvent was removed, and the crude was purified by flash chromatography (SiCh: ethyl acetate/hexane 0 to 50%) to get fert-butyl 5-bromopentanoate (3.02 g, 92%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ: 3.40 (t, 2H, J = 6.6 Hz); 2.24 (t, 2H, J = 7.3 Hz); 1.90-1.81 (m, 2H); 1.75-1.69 (m, 2H); 1.43 (s, 9H).

References:

MODERNATX, INC.;BENENATO, Kerry E.;BUTCHER, William WO2018/232120, 2018, A1 Location in patent:Paragraph 001036