Home Cart 0 Sign in  

[ CAS No. 189035-22-1 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 189035-22-1
Chemical Structure| 189035-22-1
Structure of 189035-22-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 189035-22-1 ]

Related Doc. of [ 189035-22-1 ]

SDS

Product Details of [ 189035-22-1 ]

CAS No. :189035-22-1MDL No. :MFCD08704305
Formula : C8H7BrO Boiling Point : 239.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :BQWBDYZMUCSEHK-UHFFFAOYSA-N
M.W :199.05Pubchem ID :11252616
Synonyms :

Computed Properties of [ 189035-22-1 ]

TPSA : 9.2 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.25 Rotatable Bond Count : 0

Safety of [ 189035-22-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 189035-22-1 ]

  • Upstream synthesis route of [ 189035-22-1 ]
  • Downstream synthetic route of [ 189035-22-1 ]

[ 189035-22-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 377091-18-4 ]
  • [ 189035-22-1 ]
YieldReaction ConditionsOperation in experiment
94% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4.00 h; nBuLi (2.5 M in hexane, 5.13 ml_, 12.84 mmol) was added to a -78°C cooled solution of 1 ,4-dibromo-2-(2-bronnoethoxy)benzene (3.84 g, 10.70 mmol) in THF (100 ml_). The reaction mixture was stirred at low temperature for 4 h. It was poured into H2O (100 ml_) and extracted with EtOAc (2x100 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was purified by flash chromatography on SiO2 (3percentEtOAc/hexanes) to furnish 6-bromo-2,3-dihydro-1-benzofuran (2. g, yellow solid, yield: 94percent).
85% With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1.00 h; Inert atmosphere To a solution of 1,4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene / tetrahydrofuran (28 mL, 2:5) at -78°C under N2 was added n-butyllithium (2.5 mL, 6.1 mmol). The mixture was stirred at -78°C for 1 h, and quenched by acetic acid. Water was added, and the organic layer was seperated, dried, and concentrated under vacuum to give the title compound (1.00 g, 85 percent). 1H NMR (CDCl3): δ 7.03 (1H, d, J = 8.0 Hz), 6.91-6.93 (2H, m), 4.58 (2H, t, J = 4.8 Hz), 3.15 (2H, t, J = 4.8 Hz)
85% With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1.00 h; Inert atmosphere To a solution of 1,4-dibromo-2-(2-bromoethoxy) benzene (2.13 g, 5.9 mmol) in benzene/ tetrahydrofuran (28 mL, 2:5) at −78° C. under N2 was added n-butyllithium (2.5 mL, 6.1 mmol). The mixture was stirred at −78° C. for 1 h, and quenched by acetic acid. Water was added, and the organic layer was seperated, dried, and concentrated under vacuum to give the title compound (1.00 g, 85percent). 1H NMR (CDCl3) δ7.03 (1H, d, J=8,0 Hz), 6.91-6.93 (2H, m), 4.58 (2H, t, J=4.8 Hz), 3.15 (2H, t, J=4.8 Hz).
79% With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2.50 h; Inert atmosphere 1.6 M n-Butyllithium/hexane solution (21.84 mL, 34.94 mmol) was slowly added to a solution of 1,4-dibromo-2-(2-bromoethoxy)benzene (10.45 g, 29.12 mmol) in THF (200 mL) at-78°C under argon gas atmosphere. The reaction mixture was stirred at -78°C for 30 min, and then at 0°C for 2 hr. The reaction mixture was added to ice water, and 2N hydrochloric acid was added thereto until the pH of the mixture became 3. Then, the mixture was extracted three times with a mixed solvent of ethyl acetate/hexane (3:1). The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 2→8percent ethyl acetate/hexane) to give 6-bromo-2,3-dihydrobenzofuran (4.57 g, 22.96 mmol, 79percent) as a white solid.
9.4 g With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere; Cooling To a solution of 1,4-dibromo-2-(2-bromoethoxy)benzene (22.3 g, 62.2 mmol) in THF (180 mL) was added 1.57 M n-BuLi in hexanes (40 mL, 62.8 mmol) under Ar at -76 °C.
After stirring at -76 °C overnight, the mixture was quenched with sat.
NH4Cl aq and extracted with AcOEt.
The organic phase was washed with brine and dried over Na2SO4.
After filtration and evaporation, the residue was recrystallized from ethanol (28 mL) and water (3 mL) to obtain 7 as a white solid (9.4 g, 76percent).
1H NMR (400 MHz, CDCl3) δ = 7.03 (d, J = 7.6 Hz, 1H), 6.97 (d, J = 1.6 Hz, 1H), 6.94 (dd, J = 1.6, 7.6 Hz, 1H), 4.59 (t, J = 8.8 Hz, 2H), 3.15 (t, J = 8.8 Hz, 1H); MS (ESI+) 200.1 (M+H)+.

Reference: [1] Patent: WO2009/7399, 2009, A1. Location in patent: Page/Page column 86
[2] Patent: EP2862571, 2015, A1. Location in patent: Paragraph 0146; 0147
[3] Patent: US2015/166559, 2015, A1. Location in patent: Paragraph 0200; 0201
[4] Patent: TW2016/2105, 2016, A. Location in patent: Paragraph 1108
[5] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 34
[6] Patent: US2011/263612, 2011, A1. Location in patent: Page/Page column 165
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4792 - 4803
  • 2
  • [ 377091-17-3 ]
  • [ 189035-22-1 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With phosphorus tribromide In toluene at 90℃; for 2.50 h; Heating / reflux
Stage #2: With sodium hydroxide In water; toluene at 20℃;
Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.50 h;
2-(2,5-dibromophenoxy)ethanol (4.65 g, 15.7 mmol) was dissolved in toluene (33 mL) with stirring under N2. PBr3 (0.67 mL, 7.07 mmol) was added and the resulting mixture heated at 90 0C under reflux condenser under N2 for 2.5 hours. The mixture was cooled to room temperature with a H2O bath and IN NaOH (28 mL) was added. The mixture was diluted with Et2O, shaken, and the layers separated. The organics were washed with H2O, dried over MgSO4, filtered, and concentrated on a rotary evaporator. The resulting oil was dissolved in THF (15 mL) with stirring under N2. The solution was cooled to -75 0C and n-BuLi (9.82 mL of a 1.6 M solution in hexane, 15.7 mmol) was added dropwise. The resulting clear, colorless solution was stirred 30 minutes at -75 0C, and then HOAc (1 mL) was added. The resulting mixture was warmed to room temperature and partitioned between H2O and Et2O. The organics were washed once with 0.5 M NaOH, once with H2O, and concentrated on a rotary evaporator. Flash chromatography <n="145"/>(5-10percent EtOAc/hexane) gave 1.38 g (90percent purity) (40percent yield) of 6-bromo-2,3- dihydrobenzofuran as a white solid. Rf= 0.56 (30percent EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.13 (t, J=8.52 Hz, 2 H) 4.56 (t, J=8.79 Hz, 2 H) 6.95 - 7.01 (m, 2 H) 7.14 - 7.20 (m, 1 H).
Reference: [1] Patent: WO2007/84560, 2007, A2. Location in patent: Page/Page column 143-144
[2] Patent: EP2862571, 2015, A1
[3] Patent: US2015/166559, 2015, A1
[4] Patent: TW2016/2105, 2016, A
  • 3
  • [ 496-16-2 ]
  • [ 189035-22-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 22, p. 4790 - 4798
  • 4
  • [ 1435-52-5 ]
  • [ 189035-22-1 ]
Reference: [1] Patent: EP2862571, 2015, A1
[2] Patent: US2015/166559, 2015, A1
[3] Patent: TW2016/2105, 2016, A
  • 5
  • [ 28165-52-8 ]
  • [ 189035-22-1 ]
Reference: [1] Patent: US2011/263612, 2011, A1
Historical Records

Related Functional Groups of
[ 189035-22-1 ]

Bromides

Chemical Structure| 66826-78-6

[ 66826-78-6 ]

5-Bromo-2,3-dihydrobenzofuran

Similarity: 0.98

Chemical Structure| 10016-52-1

[ 10016-52-1 ]

2,8-Dibromodibenzo[b,d]furan

Similarity: 0.94

Chemical Structure| 871888-83-4

[ 871888-83-4 ]

4-Bromo-2-ethoxy-1-methylbenzene

Similarity: 0.92

Chemical Structure| 53087-13-1

[ 53087-13-1 ]

1-(Benzyloxy)-3-bromobenzene

Similarity: 0.92

Chemical Structure| 50548-45-3

[ 50548-45-3 ]

1-Bromodibenzo[b,d]furan

Similarity: 0.90

Related Parent Nucleus of
[ 189035-22-1 ]

Aromatic Heterocycles

Chemical Structure| 10016-52-1

[ 10016-52-1 ]

2,8-Dibromodibenzo[b,d]furan

Similarity: 0.94

Chemical Structure| 206347-30-0

[ 206347-30-0 ]

7-Bromo-2,3-dihydrobenzofuran

Similarity: 0.90

Chemical Structure| 50548-45-3

[ 50548-45-3 ]

1-Bromodibenzo[b,d]furan

Similarity: 0.90

Chemical Structure| 955959-84-9

[ 955959-84-9 ]

4-(4-Bromophenyl)dibenzo[b,d]furan

Similarity: 0.90

Chemical Structure| 3875-78-3

[ 3875-78-3 ]

6-Bromochroman

Similarity: 0.90

Benzofurans

Chemical Structure| 66826-78-6

[ 66826-78-6 ]

5-Bromo-2,3-dihydrobenzofuran

Similarity: 0.98

Chemical Structure| 206347-30-0

[ 206347-30-0 ]

7-Bromo-2,3-dihydrobenzofuran

Similarity: 0.90

Chemical Structure| 1392072-52-4

[ 1392072-52-4 ]

6-Bromo-2,3-dihydrobenzofuran-3-ol

Similarity: 0.89

Chemical Structure| 39178-60-4

[ 39178-60-4 ]

5-Bromo-2-ethylbenzofuran

Similarity: 0.85

Chemical Structure| 128851-73-0

[ 128851-73-0 ]

6-Bromobenzofuran

Similarity: 0.85