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189035-22-1

Basic Information
CAS No.: 189035-22-1
Name: 6-BROMO-2,3-DIHYDRO-BENZOFURAN
Article Data: 12
Molecular Structure:
Molecular Structure of 189035-22-1 (6-BROMO-2,3-DIHYDRO-BENZOFURAN)
Formula: C8H7 Br O
Molecular Weight: 199.047
Synonyms: 6-Bromo-2,3-dihydro-1-benzofuran;6-Bromo-2,3-dihydrobenzofuran
Density: 1.582g/cm3
Boiling Point: 239.8°C at 760 mmHg
Flash Point: 94.9°C
PSA: 9.23000
LogP: 2.38400
Synthetic route
377091-18-4

1,4-dibromo-2-(2-bromoethoxy)benzene

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4h;94%
With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1h; Inert atmosphere;85%
With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1h; Inert atmosphere;85%
377091-17-3

1,4-dibromo-2-hydroxyethoxybenzene

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
Stage #1: 1,4-dibromo-2-hydroxyethoxybenzene With phosphorus tribromide In toluene at 90℃; for 2.5h; Heating / reflux;
Stage #2: With sodium hydroxide In water; toluene at 20℃;
Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.5h;
40%
Multi-step reaction with 2 steps
1: phosphorus tribromide / toluene / 10 h / 90 °C
2: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: phosphorus tribromide / toluene / 2.5 h / 20 - 90 °C
2: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C / Inert atmosphere
View Scheme
496-16-2

2,3-Dihydrobenzofuran

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
With potassium hydroxide; bromine; potassium bromide at 20℃;

2-trimethylstannyl-1,3-cyclohexadiene

Br2 -solution

Br2 -solution

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
In n-heptane; dichloromethane; ethyl acetate
28165-52-8

2,5-dibromophenol

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / 40 h / 80 °C
2: n-butyllithium / hexane; tetrahydrofuran / 4 h / -78 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 4 h / 80 °C
2: n-butyllithium / tetrahydrofuran / 3 h / -100 °C
View Scheme
1435-52-5

2,5-dibromofluorobenzene

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-methyl-pyrrolidin-2-one; potassium tert-butylate / 100 °C / Inert atmosphere
2: phosphorus tribromide / toluene / 10 h / 90 °C
3: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 100 °C / Inert atmosphere
2: phosphorus tribromide / toluene / 10 h / 90 °C
3: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate; 1-methyl-pyrrolidin-2-one / 15 h / 20 - 100 °C
2: phosphorus tribromide / toluene / 2.5 h / 20 - 90 °C
3: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C / Inert atmosphere
View Scheme
189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

1102467-17-3

5,6-dibromo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h;93%
With N-Bromosuccinimide In acetonitrile at 20℃;

potassium cyanide

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

C9H7NO

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube;
Stage #2: 6-bromo-2,3-dihydro-1-benzofuran With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;
93%
189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

496047-46-2

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine

721965-55-5

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine

Conditions
ConditionsYield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran
Stage #2: 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine In tetrahydrofuran at -78℃; for 1h; Grignard reaction;
89%
68-12-2, 33513-42-7

N,N-dimethyl-formamide

189035-22-1

6-bromo-2,3-dihydro-1-benzofuran

55745-96-5

2,3-dihydro-1-benzofuran-6-carbaldehyde

Conditions
ConditionsYield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In 2-methyltetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran; hexane at -78℃; for 2h;
85%
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 0.75h;
79%
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
52%
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