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Chemical Structure| 20776-50-5 Chemical Structure| 20776-50-5
Chemical Structure| 20776-50-5

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Synonyms: 4-Bromoanthranilic Acid

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Product Details of 2-Amino-4-bromobenzoic acid

CAS No. :20776-50-5
Formula : C7H6BrNO2
M.W : 216.03
SMILES Code : C1=C(C(=CC(=C1)Br)N)C(=O)O
Synonyms :
4-Bromoanthranilic Acid
MDL No. :MFCD03618454
InChI Key :BNNICQAVXPXQAH-UHFFFAOYSA-N
Pubchem ID :88691

Safety of 2-Amino-4-bromobenzoic acid

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

Application In Synthesis of 2-Amino-4-bromobenzoic acid

* 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.

  • Upstream synthesis route of [ 20776-50-5 ]
  • Downstream synthetic route of [ 20776-50-5 ]

[ 20776-50-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 20776-50-5 ]
  • [ 917-54-4 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
33% at -78℃; for 1 h; To a -78 °C solution of 2-amino-4-bromobenzoic acid (2.16 g, 10 mmol) in THF (20 mL) was added MeLi (13.3 mL, 3M, 0.04 mmol). The resulting reaction was allowed to stir at -78 °C for 1 hour, then was quenched with water and extracted with EtOAc. The organic extract was dried over anhydrous Na2S04, filtered and concentrated in vacuo and the resulting residue was purified using flash chromatography on silica gel to provide Int-21 (700 mg, 33 percent). 1H NM (CDC13): δ 7.51 - 7.58 (m, 1 H), 6.72 - 6.84 (m, 2 H), 6.37 (s, 2 H), 7.73 (s, 2 H). MS (ESI) m/e (M+H*): 214.
References: [1] Patent: WO2012/50848, 2012, A1, . Location in patent: Page/Page column 121.
  • 2
  • [ 20776-50-5 ]
  • [ 98-80-6 ]
  • [ 4445-43-6 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16 h; Inert atmosphere 2. i. 3 -amino- [ 1, 1 '-biphenylj -4-carboxylic acid:
To a mixture of 2-amino-4-bromobenzoic acid (0.992 g; 4.46 mmol), phenylboronic acid (0.832 g; 6.69 mmol) and Pd(PPh3)4 (0.052 g; 0.045 mmol) under nitrogen was added degassed DMF (10 mL) and aq. \M K2C03 (7 mL). The resulting mixture was stirred at 80°C for 16 h. DMF was removed under reduced pressure. The residue was taken up in 4N NaOH (40 mL) and the aq. phase was washed twice with EA (2 x 50 mL). The pH of the aq. layer was adjusted to 5 by addition of 4N HC1. The aq. phase was extracted three times with EA (3 x 50 mL) and once with DCM-MeOH 9-1 (50 mL). The combined org. layers were dried over MgS04 and evaporated under reduced pressure to give a beige solid. It was triturated in Et20, filtered and dried to give the title compound as a beige solid (0.721 g; 76percent yield). MS (ESI, m/z): 214.3 [M+H+] for Ci3HnN02; tR = 0.78 min.
References: [1] Patent: WO2015/173329, 2015, A1, . Location in patent: Page/Page column 99.
  • 3
  • [ 20776-50-5 ]
  • [ 20776-54-9 ]
References: [1] Patent: WO2008/154642, 2008, A2, . Location in patent: Page/Page column 182.
  • 4
  • [ 20776-50-5 ]
  • [ 56-81-5 ]
  • [ 928839-62-7 ]
References: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231.
 

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