111771-12-1|2-Fluoro-6-iodobenzoyl chloride| Ambeed

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Quality Control of [ 111771-12-1 ] Purity: 98% SDS Specification

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Product Details of [ 111771-12-1 ]

CAS No. :	111771-12-1
Formula :	C₇H₃ClFIO
M.W :	284.45
SMILES Code :	O=C(Cl)C1=C(I)C=CC=C1F
MDL No. :	MFCD03094410
InChI Key :	KUULKUHCAMRGCF-UHFFFAOYSA-N
Pubchem ID :	2778660

Safety of [ 111771-12-1 ]

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Signal Word:	Danger
Hazard Statements:	H314
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Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of [ 111771-12-1 ]

* 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 [ 111771-12-1 ]

[ 111771-12-1 ] Synthesis Path-Downstream 1~2

1
[ 111771-08-5 ]
[ 111771-12-1 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0℃;	To a heterogeneous mixture of <strong>[111771-08-5]2-fluoro-6-iodobenzoic acid</strong> (1 .51 g, 5.66 mmol) at 0 C in DCM (28 mL) was added oxalyl chloride (0.635 mL, 7.36 mmol) followed by DMF (0.15 mL). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (28 mL) and treated with solid N-hydroxyacetamidine (503 mg, 6.79 mmol) in several portions followed by TEA (1 .2 mL, 8.49 mmol) at 0 C. After stirring for 14 h at ambient temperature the mixture was washed with saturated aqueous NaHCO3 solution. The combined organic extracts were dried over Na2SO4, filtered andconcentrated in vacuo. Chromatography (Hex to 100% EtOAc/Hex) afforded the desired product as a colorless oil (1 .57 g, 86%). MS (ESI) mass calculated for C9H8FIN2O2, 321 .96; m/z found, 323.0. 1 H NMR (500 MHz, CDCI3): 7.70 - 7.65 (m, 1 H), 7.15 - 7.1 1 (m, 2H), 4.87 (br s, 2H), 2.06 (s, 3H).
	With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃;	Step A: (Z)-N'-((2-Fluoro-6-iodobenzoyl)oxy)acetimidamide. To a heterogeneous mixture of <strong>[111771-08-5]2-fluoro-6-iodobenzoic acid</strong> (1 .51 g, 5.66 mmol) at 0 C in DCM (28 mL) was added oxalyl chloride (0.635 mL, 7.36 mmol) followed by DMF (0.15 mL). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (28 mL) and treated with solid N-hydroxyacetamidine (503 mg, 6.79 mmol) in several portions followed by TEA (1 .2 mL, 8.49 mmol) at 0 C. After stirring for 14 h at ambient temperature the mixture was washed with saturated aqueous NaHCO3 solution. The combined organic extracts were dried over Na2SO4, filtered andconcentrated in vacuo. Chromatography (Hex to 100% EtOAc/Hex) afforded the desired product as a colorless oil (1 .57 g, 86%). MS (ESI) mass calculated for C9H8FIN2O2, 321 .96; m/z found, 323.0. 1 H NMR (500 MHz, CDCI3): 7.70 - 7.65 (m, 1 H), 7.15 - 7.1 1 (m, 2H), 4.87 (br s, 2H), 2.06 (s, 3H).
	With oxalyl dichloride; In dichloromethane; at 20℃; for 1h;Inert atmosphere;	Oxalyl chloride (2.5 ml, 28.66 mmol, 1.5 eq.) was added at room temperature to a suspension of <strong>[111771-08-5]2-fluoro-6-iodobenzoic acid</strong> (5.1 g, 19.17 mmol, 1 eq.) in 40 ml of dry DCM under nitrogen atmosphere. A few drops of dry DMF were added and the mixture was stirred at room temperature for 1 h. The solvent was removed by distillation. The obtainedresidue was taken up in acetonitrile, which was distilled again, to remove excess acidity. The resulting brown oil was dissolved in dry DCM and the resulting solution was drop- wise added to a suspension of potassium carbonate (7g, 50.6mmol, 2.6 eq.) in 20 ml of dry methanol. The reaction mixture was then stirred at room temperature overnight.The next morning the solids were filtered away and washed with DCM. The volume of theliquid phase was reduced by vacuum distillation. The resulting slurry was taken up inDCM and filtered again.The clear liquid phase was then dried over sodium sulphate, filtered and evaporated dodryness to give 4.27 g (15.25 mmol) of (D77) as a yellow oil.MS (ESI) mlz: 219 [M+H].1H NMR (ODd3) 5 ppm = 7.78 -7.60 (m, 1 H), 7.28 (s, 1 H), 7.14 (dd, J = 3.7, 8.1 Hz, 2 H), 4.00 (s, 3 H).

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere;

Oxalyl chloride (2.5 ml, 28.66 mmol, 1.5 eq.) was added at room temperature to a suspension of <strong>[111771-08-5]2-fluoro-6-iodobenzoic acid</strong> (5.1 g, 19.17 mmol, 1 eq.) in 40 ml of dry DCM under nitrogen atmosphere. A few drops of dry DMF were added and the mixture was stirred at room temperature for 1 h. The solvent was removed by distillation. The obtained residue was taken up in acetonitrile, which was distilled again, to remove excess acidity. The resulting brown oil was dissolved in dry DCM and the resulting solution was dropwise added to a suspension of potassium carbonate (7 g, 50.6 mmol, 2.6 eq.) in 20 ml of dry methanol. The reaction mixture was then stirred at room temperature overnight. The next morning the solids were filtered away and washed with DCM. The volume of the liquid phase was reduced by vacuum distillation. The resulting slurry was taken up in DCM and filtered again. The clear liquid phase was then dried over sodium sulphate, filtered and evaporated do dryness to give 4.27 g (15.25 mmol) of (D77) as a yellow oil. MS (ESI) m/z: 219 [M+H]+. 1H NMR (CDCl3) delta ppm=7.78-7.60 (m, 1H), 7.28 (s, 1H), 7.14 (dd, J=3.7, 8.1 Hz, 2H), 4.00 (s, 3H).

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 345 - 352.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 272 - 282.
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 3047 - 3062.
[4]Patent: WO2011/50200,2011,A1 .Location in patent: Page/Page column 87.
[5]Patent: WO2011/50202,2011,A1 .Location in patent: Page/Page column 59.
[6]Patent: WO2013/92893,2013,A1 .Location in patent: Page/Page column 44; 45.
[7]Patent: US2014/357653,2014,A1 .Location in patent: Paragraph 0280; 0281; 0282; 0283; 0284; 0285.
[8]Organic Letters,2019,vol. 21,p. 9960 - 9964.
[9]Journal of Medicinal Chemistry,2019,vol. 62,p. 10221 - 10244.

2
[ 67-56-1 ]
[ 111771-12-1 ]
[ 146014-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; N,N-dimethyl-formamide;	Step A: (Z)-N'-((2-Fluoro-6-iodobenzoyl)oxy)acetimidamide. To a heterogeneous mixture of 2-fluoro-6-iodobenzoic acid (1 .51 g, 5.66 mmol) at 0 C in DCM (28 mL) was added oxalyl chloride (0.635 mL, 7.36 mmol) followed by DMF (0.15 mL). Gas evolution commenced immediately and after 5 min the ice bath was removed. When gas evolution had ceased and the mixture was homogeneous an aliquot was removed and quenched with MeOH. Formation of the methyl ester was confirmed by HPLC and the mixture was concentrated in vacuo. The viscous liquid was dissolved in fresh DCM (28 mL) and treated with solid N-hydroxyacetamidine (503 mg, 6.79 mmol) in several portions followed by TEA (1 .2 mL, 8.49 mmol) at 0 C. After stirring for 14 h at ambient temperature the mixture was washed with saturated aqueous NaHCO3 solution. The combined organic extracts were dried over Na2SO4, filtered andconcentrated in vacuo. Chromatography (Hex to 100% EtOAc/Hex) afforded the desired product as a colorless oil (1 .57 g, 86%). MS (ESI) mass calculated for C9H8FIN2O2, 321 .96; m/z found, 323.0. 1 H NMR (500 MHz, CDCI3): 7.70 - 7.65 (m, 1 H), 7.15 - 7.1 1 (m, 2H), 4.87 (br s, 2H), 2.06 (s, 3H).
4.27 g	With potassium carbonate; In dichloromethane; at 20℃;	Oxalyl chloride (2.5 ml, 28.66 mmol, 1.5 eq.) was added at room temperature to a suspension of 2-fluoro-6-iodobenzoic acid (5.1 g, 19.17 mmol, 1 eq.) in 40 ml of dry DCM under nitrogen atmosphere. A few drops of dry DMF were added and the mixture was stirred at room temperature for 1 h. The solvent was removed by distillation. The obtainedresidue was taken up in acetonitrile, which was distilled again, to remove excess acidity. The resulting brown oil was dissolved in dry DCM and the resulting solution was drop- wise added to a suspension of potassium carbonate (7g, 50.6mmol, 2.6 eq.) in 20 ml of dry methanol. The reaction mixture was then stirred at room temperature overnight.The next morning the solids were filtered away and washed with DCM. The volume of theliquid phase was reduced by vacuum distillation. The resulting slurry was taken up inDCM and filtered again.The clear liquid phase was then dried over sodium sulphate, filtered and evaporated dodryness to give 4.27 g (15.25 mmol) of (D77) as a yellow oil.MS (ESI) mlz: 219 [M+H].1H NMR (ODd3) 5 ppm = 7.78 -7.60 (m, 1 H), 7.28 (s, 1 H), 7.14 (dd, J = 3.7, 8.1 Hz, 2 H), 4.00 (s, 3 H).
4.27 g	With potassium carbonate; In dichloromethane; at 20℃;	Oxalyl chloride (2.5 ml, 28.66 mmol, 1.5 eq.) was added at room temperature to a suspension of 2-fluoro-6-iodobenzoic acid (5.1 g, 19.17 mmol, 1 eq.) in 40 ml of dry DCM under nitrogen atmosphere. A few drops of dry DMF were added and the mixture was stirred at room temperature for 1 h. The solvent was removed by distillation. The obtained residue was taken up in acetonitrile, which was distilled again, to remove excess acidity. The resulting brown oil was dissolved in dry DCM and the resulting solution was dropwise added to a suspension of potassium carbonate (7 g, 50.6 mmol, 2.6 eq.) in 20 ml of dry methanol. The reaction mixture was then stirred at room temperature overnight. The next morning the solids were filtered away and washed with DCM. The volume of the liquid phase was reduced by vacuum distillation. The resulting slurry was taken up in DCM and filtered again. The clear liquid phase was then dried over sodium sulphate, filtered and evaporated do dryness to give 4.27 g (15.25 mmol) of (D77) as a yellow oil. MS (ESI) m/z: 219 [M+H]+. 1H NMR (CDCl3) δ ppm=7.78-7.60 (m, 1H), 7.28 (s, 1H), 7.14 (dd, J=3.7, 8.1 Hz, 2H), 4.00 (s, 3H).

References: [1]Patent: WO2011/50202,2011,A1 .Location in patent: Page/Page column 59.
[2]Patent: WO2013/92893,2013,A1 .Location in patent: Page/Page column 44; 45.
[3]Patent: US2014/357653,2014,A1 .Location in patent: Paragraph 0280; 0281; 0282; 0283; 0284; 0285.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Passerini Reaction • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Dihalides • Rosenmund Reduction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 111771-12-1 ]

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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 111771-12-1

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