881415-27-6|2-Bromo-3-fluoro-6-nitrobenzoic acid| Ambeed

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Quality Control of [ 881415-27-6 ] Purity: 98% SDS Specification

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Product Details of [ 881415-27-6 ]

CAS No. :	881415-27-6
Formula :	C₇H₃BrFNO₄
M.W :	264.01
SMILES Code :	O=C(O)C1=C([N+]([O-])=O)C=CC(F)=C1Br
MDL No. :	MFCD27931341
InChI Key :	WHOTUUFDHGVXSG-UHFFFAOYSA-N
Pubchem ID :	59849177

Safety of [ 881415-27-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 881415-27-6 ]

* 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 [ 881415-27-6 ]

[ 881415-27-6 ] Synthesis Path-Downstream 1~19

1
[ 132715-69-6 ]
[ 881415-28-7 ]
[ 881415-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid; at 0 - 20℃; for 2.16667h;	Example 9: methyl 3-((2R)-l-(2-(3,4-dimethoxyphenyl)-2-(7-fluoro-3- oxoisoindolin-5-ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate[00234] In a 50 mL round-bottomed flask 2-bromo-3-fluoro-benzoic acid (5 g,22.8 mmol) and sulfuric acid (15 mL) were stirred at 0 0C before adding fuming nitric acid (2 mL, 22.83 mmol, 90%) drop wise over 10 min. The reaction was stirred for 2 h at rt. The reaction was poured onto ice and the solids were isolated by filtration. The crude solids were purified on SiO2 (eluting with 0-100% EtOAc) to yield a 1: 1 mixture of region-isomers 9A and 2-bromo-3-fluoro-6-nitrobenzoic acid (3.7g, 63% yield). 1H NMR (400 MHz, CD3OD) delta ppm 7.48 (dd, J=9.23, 7.47 Hz, 1 H) 8.16 (dd, J=7.91, 2.64 Hz, 1 H) 8.26 (dd, J=9.23, 4.39 Hz, 1 H) 8.35 - 8.40 (m, 1 H).
	With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 1.5h;	In a 1 L, three necked, round-bottomed flask fitted with a dropping funnel and a thermometer were charged 33 g (0.15 mol) of 2-bromo-3-fluoro-benzoic acid and 200 mL of concentrated sulfuric acid. After cooling to 0 C., 16 mL of HNO3 (70%) was added dropwise over 30 min keeping temperature at 10 or less degrees. After 1 h, the reaction mixture was poured into the crushed ice keeping temperature at 20 or less degrees. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give a mixture of 2-bromo-3-fluoro-6-nitro-benzoic acid and 2-bromo-3-fluoro-5-nitro benzoic acid (2:1) as brown solids in quantitative yield. 1H-NMR (400 MHz, CDCl3, delta, ppm) 2-bromo-3-fluoro-6-nitro-benzoic acid: 7.37 (dd, 1H), 8.27 (dd, 1H), 2-bromo-3-fluoro-5-nitro benzoic acid:
	With sulfuric acid; nitric acid; at 0℃; for 1.5h;	A solution of 2-bromo-3-fluorobenzoic acid (CAS registry 132715-69-6) (5 g, 22.83 mmol) inH2S04 conc. (15.82 ml, 297 mmol ) was cooled to 0C and was treated dropwise with fumingHNO3 (1.36 ml, 27.4 mmol). A white precipitate was formed. The resulting suspension wasstirred at 0C for 1.5 h. The mixture was poured onto ice water and stirred for 30 mm. Theresulting mixture was diluted with water and extracted with DCM. Then, the organic phases were dried over Na2SO4 and concentrated under reduced pressure. This afforded an off- white solid (5.67 g, 94%) of a mixture of 2-bromo-3-fluoro-6-nitrobenzoic acid (regioisomer 1) and 2-bromo-3-fluoro-5-nitrobenzoic acid (regioisomer 2) in a ratio of ca. 2:1, which wasused without separation for the next step.HPLC 1st regioisomer (69%) Rt= 0.33 mm; HPLC 2? regioisomer (30%) Rt= 0.52 mm.

With sulfuric acid; nitric acid; In water; at 20℃; for 2h;

In an ice bath, fuming nitric acid (2mL, 22.83mmoL) was added dropwise 2-bromo-3-fluoro - benzoic acid (5g, 22.8mmol) and concentrated sulfuric acid (15mL) in the mixed solution.After the addition was complete, brought to room temperature stirred for 2 hours.Poured into ice water, a large number of solid was filtered, the solid washed with water and dried under high vacuum, a white solid 5.3g, mixture of intermediate 4c and 4e, (4c / 4e = 2/1), in a yield of 88%.Most of this mixture was used directly in the next reaction, a small amount was purified by column chromatography and identified as follows:

References: [1]Patent: WO2008/79759,2008,A1 .Location in patent: Page/Page column 106.
[2]Patent: US2008/293708,2008,A1 .Location in patent: Page/Page column 38.
[3]Patent: WO2015/10641,2015,A1 .Location in patent: Page/Page column 127.
[4]Patent: CN103804358,2016,B .Location in patent: Paragraph 0156.

2
[ 67-56-1 ]
[ 881415-28-7 ]
[ 881415-27-6 ]
[ 1036389-05-5 ]
[ 1036390-96-1 ]

Yield	Reaction Conditions	Operation in experiment
		9A (3.7g, 14 mmol) was refluxed for 1 h in thionyl chloride (15 mL) and concentrated to an oil. MeOH (40 mL) was added slowly to the residue and the mixture refluxed for 1 h. The reaction was concentrated to dryness. The residue was heated at 90 0C for 4 h in acetic acid (20 mL) with a Fe powder (365 mg, 6.7 mmol). Upon cooling to rt the reaction was diluted with EtOAc (100 mL) and the resulting mixture filtered through Celite . The filter cake was washed with EtOAc (3 x 100 mL). The combined organics were washed with water and brine, dried w/ MgSO4 and concentrated to give 9B (2.Og, 54% yield) in a 1: 1 mixture with a regioisomers. MS (ESI) mk 248.1 (M+H)

References: [1]Patent: WO2008/79759,2008,A1 .Location in patent: Page/Page column 106-107.

3
[ 881415-28-7 ]
[ 881415-27-6 ]
[ 74-88-4 ]
[ 881415-30-1 ]
[ 881415-29-8 ]