3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one

Base Information

• Chemical Name: 3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one
• CAS No.: 1378390-29-4
• Molecular Formula: C19H15BrO3
• Molecular Weight: 371.23
• Mol file: 1378390-29-4.mol

Synonyms:3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one;3-(2-Bromo-acetyl)-10,11-dihydro-5H,9H-6-oxa-benzo[a]anthracen-8-one;3-(2-Bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one 3-(2-Bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one ;3-(2-Bromoacetyl)-10,11-dihydro-5h-dibenzo[c,g]chromen-8(9h)-on

Chemical Property of 3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one

Chemical Property:

• Boiling Point: 578.6±50.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.514±0.06 g/cm3(Predicted)
• LogP: 4.34260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

3-(2-Bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(2-Bromoacetyl)-10,11-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-8(9H)-one is an antiviral agent and Velpatasvir (V116000) intermediate. Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection.

Technology Process of 3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one

There total 6 articles about 3-(2-bromoacetyl)-10,11-dihydro-5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one 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: 56.0%

3-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (1378391-36-6) → 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (1378390-29-4)

Guidance literature:

3-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one; With N-Bromosuccinimide; In tetrahydrofuran; water; dimethyl sulfoxide; at 20 ℃; for 0.55h;

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 15h;

Reference yield:

7-hydroxy-1-tetralone (22009-38-7) → 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (1378390-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

2.1: Trimethylacetic acid; potassium carbonate; palladium(II) trimethylacetate; P(p-C₆H₄F)3 / N,N-dimethyl acetamide / 24 h / 60 °C / Inert atmosphere

3.1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate / propan-1-ol / 5.5 h / Inert atmosphere; Reflux

4.1: N-Bromosuccinimide / water; tetrahydrofuran; dimethyl sulfoxide / 0.55 h / 20 °C

4.2: 15 h / 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; N-Bromosuccinimide; palladium(II) trimethylacetate; palladium diacetate; potassium carbonate; P(p-C₆H₄F)3; Trimethylacetic acid; In tetrahydrofuran; propan-1-ol; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

3-(2-bromo-1-hydroxyethyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (1378391-38-8) → 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (1378390-29-4)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 15h;

upstream raw materials:

3-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

7-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalene-1(2H)-one

7-hydroxy-1-tetralone

2-bromo-5-chlorobenzyl bromide

Downstream raw materials:

(2S,5S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 5-methylpyrrolidine-1,2-dicarboxylate

(2S,4S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-methylpyrrolidine-1,2-dicarboxylate

(2S,4S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

(2R,4R)-1-tert-butyl 2-(2-(9-((2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

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