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Home > Encyclopedia > 3-BROMO-2-FLUOROPHENYLBORONIC ACID

3-BROMO-2-FLUOROPHENYLBORONIC ACID

3-BROMO-2-FLUOROPHENYLBORONIC ACID structure

3-BROMO-2-FLUOROPHENYLBORONIC ACID 

structure
  • CAS No:

    352535-97-8

  • Formula:

    C6H5BBrFO2

  • Chemical Name:

    3-BROMO-2-FLUOROPHENYLBORONIC ACID

  • Synonyms:

    3-BroMo-2-fluorobenzeneboronic acid, 98%;3-Bromo-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)

  • Categories:

    Organic Chemistry  >  Organic Fluorine Compound

3-BROMO-2-FLUOROPHENYLBORONIC ACID Basic Attributes

218.82

217.95500

DTXSID90584268

2931900090

Characteristics

40.5

0.26800

Solid

1.75 g/cm3

225-227 °C(lit.)

326.6°C at 760 mmHg

151.3ºC

Safety Information

NONH for all modes of transport

3

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

3-BROMO-2-FLUOROPHENYLBORONIC ACID Use and Manufacturing

Methods of Manufacturing

(3-Bromo-2-fluorophenyl)boronic acid (30.0 g, 137 mmol) and 2, 4-dichloro-6-iodophenol (43.6 g, 150 mmol) were added to 400 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (56.8 g, 411 mmol) was added by dissolving in 150 ml of water and thoroughly stirred. Tetrakistriphenyl-phosphinopalladium (4.8 g, 4 mmol) was then added thereto. After reaction for 12 hours, the temperature was lowered to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was dried, and then subjected to column chromatography with hexane and ethyl acetate to give Compound 4'A (36.9 g, 80%).To a schlenck flask was added Similar to as described in General Procedure X, 2-chloropyrimidine-4-carboxamide was reactedwith To 5-chloro-2-fluoro-4-iodopyridine (400 mg, 1.554 mmol) was added 3-bromo-2- fluorophenylboromc acid (340 mg, 1.554 mmol), PdCl2(dppf).CH2C12 adduct (127 mg, 0.155 mmol), DME (6.8 ml) and last 2M sodium carbonate (2.331 ml, 4.66 mmol). The reaction was stirred at 85 C for 3 hr. The reaction was followed by LCMS. The reaction was cooled, 15 ml of ethyl acetate and 5 ml of methanol was added, filtered and concentrated to crude product. The crude was purified by silica gel chromatography using 40g column eluting with 0%-10% ethyl acetate with heptane. The desired fractions were concentrated to constant mass, giving 250 mg of the titled compound as free base used without further purification. LCMS (m/z): 304.0/306.0 (MH+), rt = 1.07 mm.

Uses

suzuki reaction

Computed Properties

Molecular Weight:218.82
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:217.95500
Monoisotopic Mass:217.95500
Topological Polar Surface Area:40.5
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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