Tert-butyl 2-(bromomethyl)benzoate

Base Information

• Chemical Name: Tert-butyl 2-(bromomethyl)benzoate
• CAS No.: 105340-30-5
• Molecular Formula: C12H15BrO2
• Molecular Weight: 271.154
• DSSTox Substance ID: DTXSID70466619
• Nikkaji Number: J1.462.580A
• Wikidata: Q82293213
• Mol file: 105340-30-5.mol

Synonyms:Tert-butyl 2-(bromomethyl)benzoate;105340-30-5;2-(bromomethyl)benzoic acid t-butyl ester;Benzoic acid, 2-(bromomethyl)-, 1,1-dimethylethyl ester;SCHEMBL319240;DTXSID70466619;CZZWLGQCYJDGCR-UHFFFAOYSA-N;Tert-butyl2-(bromomethyl)benzoate;MFCD16620832;AKOS030627693;AM85464;2-(bromomethyl)benzoic acid t-butylester;AS-30376;EN300-7353363

Chemical Property of Tert-butyl 2-(bromomethyl)benzoate

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 270.02554
• Heavy Atom Count: 15
• Complexity: 220

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CC=CC=C1CBr

Technology Process of Tert-butyl 2-(bromomethyl)benzoate

There total 5 articles about Tert-butyl 2-(bromomethyl)benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

tert-butyl 2-methylbenzoate (16537-18-1) → 2-(bromomethyl)benzoic acid t-butyl ester (105340-30-5)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; for 1h; Inert atmosphere; Reflux;

DOI:10.1039/c1ob05506b

Reference yield: 77.0%

tert-butyl 2,2,2-trichloroacetimidate (15679-00-2) + 2-(bromomethyl)benzoic acid (7115-89-1) → 2-(bromomethyl)benzoic acid t-butyl ester (105340-30-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃;

DOI:10.1016/S0040-4039(00)02032-3

Reference yield:

2-Methyl-benzoic acid methyl ester (89-71-4) → 2-(bromomethyl)benzoic acid t-butyl ester (105340-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / tetrahydrofuran / Inert atmosphere

2: N-Bromosuccinimide / dichloromethane / 1 h / Inert atmosphere; Reflux

With N-Bromosuccinimide; potassium tert-butylate; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c1ob05506b

upstream raw materials:

tert-butyl 2,2,2-trichloroacetimidate

2-(bromomethyl)benzoic acid

tert-butyl 2-methylbenzoate

ortho-methylbenzoic acid

Downstream raw materials:

2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid

2-(1,4,7,10,13pentaoxa-cyclopentadec-2-ylmethoxymethyl)-benzoic acid tert-butyl ester

2-(1,4,7,10tetraoxa-cyclododec-2-ylmethoxymethyl)-benzoic acid tert-butyl ester

2-(1,4,7,10,13,16hexaoxa-cyclooctadec-2-ylmethoxymethyl)-benzoic acid tert-butyl ester