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Chemical Structure| 111758-64-6 Chemical Structure| 111758-64-6

Structure of 111758-64-6

Chemical Structure| 111758-64-6

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Product Details of [ 111758-64-6 ]

CAS No. :111758-64-6
Formula : C9H9BrO3
M.W : 245.07
SMILES Code : O=C(OC)COC1=CC=CC(Br)=C1
MDL No. :MFCD00461100
InChI Key :MYPHYUYCJZVEDV-UHFFFAOYSA-N
Pubchem ID :13827038

Safety of [ 111758-64-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 111758-64-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 111758-64-6 ]

[ 111758-64-6 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 591-20-8 ]
  • [ 96-32-2 ]
  • [ 111758-64-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; In acetonitrile; at 50.0℃; Intermediate 5. (3-Bromo-phenoxy)-acetic acid methyl ester.[0059] 3-Bromo-phenol (1.72 g, 10 mmol) together with methyl-bromoacetate(1.01 mL, 11 mmol) are dissolved in MeCN (600 mL). K2CO3 (2.07 g, 15 mmol) is added and the mixture is stirred at 500C overnight. After insoluble salts are filtered and washed with MeCN, the solvent is removed and the remainder is taken up in EtOAc and washed subsequently with water and brine. The organic layer is dried (MgSO4), filtered and concentrated to afford 5 (2.31 g, 95%) as a colourless semi-solid: MS calcd. for C9HioBrθ3 (MH-H+) 245.0, found 244.9.
80% With sodium iodide; In tetrahydrofuran; water; mineral oil; 1 Methyl 3-bromophenoxyacetate A solution of 3-bromophenol (17.3 g, 100 mmol) in 30 ml of THF is added at ambient temperature to a 50% solution of sodium hydride dispersed in mineral oil (5 g, 125 mmol) in 50 ml of anhydrous THF. The mixture was stirred at ambient temperature for 30 minutes before successively adding a solution of methyl bromoacetate (10.4 ml, 110 mmol) in 33 ml of anhydrous THF and sodium iodide (3.75 g, 25 mmol). The reaction medium is stirred for 30 minutes at ambient temperature and then treated with 30 ml of water at 0 C. The raw product is purified by chromatography on silica (eluent petroleum ether:ether 100:10). 19.66 g of methyl 3-bromophenoxyacetate is obtained (yield=80%). M. Pt. ( C.)=39. NMR1H 200 MHz (CDCl3): 3.75 (s, 3H, MeO); 4.57 (s, 2H, CH2-O); 6.75-6.85 (m, 1H, ArH); 7.00-7.25 (m, 3H, ArH).
With potassium carbonate; In acetonitrile; at 50.0℃; Intermediate 43. (3-Bromo-phenoxy)-acetic acid methyl ester.[0037] 3-Bromo-phenol 42 (1.72 g, 10 mmol) together with methyl-bromoacetate(1.01 inL, 11 mmol) are dissolved in MeCN (600 mL). K2CO3 (2.07 g, 15 mmol) is added and the mixture is stirred at 50C overnight. After insoluble salts are filtered and washed with MeCN5 the solvent is removed and the remainder is taken up in EtOAc and washed subsequently with water and brine. The organic layer is dried (MgSO4), filtered and <n="39"/>concentrated to afford 43 as a colorless semi-solid: MS calcd. for C9HiOBrO3 (JVH-H+) 245.0, found 244.9
With potassium carbonate; In acetone; A mixture of methyl (3-bromophenoxy) acetate (1.29 g, 5 mmol), prepared from 3-bromophenol, methyl bromoacetate, and potassium carbonate in acetone, 4- boronobenzoic acid [(1.] 25 g, 7. 5 mmol), triethylamine (2. [1] mL, 15 mmol), palladium acetate (33.5 mg), and tri-o-tolylphosphine (95 mg) in dry dimethylformamide (20 mL) was heated to [100C] for 3.5 h, cooled, and concentrated in vacuo. The residue was taken up in water, extracted with ethyl acetate and then with dichloromethane. The combined dichloromethane extract was concentrated in vacuo to give the title compound.
With potassium carbonate; In acetonitrile; at 50.0℃; To a solution of 3-bromophenol (1.72 g, 10.0 mmol) and methyl-bromoacetate (1.01 mL, 1 1.0 mmol) in ACN (60 mL) was added K2C03 (2.07 g, 15.0 mmol) and the mixture was stirred at 50C overnight After insoluble salts are filtered off and washed with ACN, the solvent is removed under reduced pressure and the remainder is taken up in EA and washed subsequently with water and brine. The organic layer is dried over Na2S04, filtered and concentrated to give compound P10 as a colorless semi-solid.

  • 3
  • [ 111758-64-6 ]
  • [ 1798-99-8 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride; lithium hydroxide monohydrate; In tetrahydrofuran-water; 2) 3-bromophenoxyacetic acid. At 0 C., lithium hydroxide monohydrate (8.41 g, 0.2 mol) is added to a solution of methyl 3-bromophenoxyacetate (19.66 g, 80 mmol) in solution in 100 ml of a water-THF mixture (3:1). Agitation is continued for 15 minutes at 0 C. and then the mixture is acidified by a 3N aqueous solution of hydrochloric acid. It is extracted with ether, dried over MgSO4, filtered and evaporated. 18.21 g of 3-bromophenoxyacetic acid is obtained (yield=98%). M.Pt. ( C.)=108. NMR1H 200 MHz (CDCl3): 4.70 (s, 2H, CH2-O); 6.80-6.90 (1H, ArH); 7.05-7.10 (m, 1H, ArH); 7.15-7.20 (m, 2H, ArH); 9.40-9.05 (m, 1H, mobile H).
 

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