103438-86-4|2-Fluoro-3-hydroxybenzaldehyde| Ambeed

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Quality Control of [ 103438-86-4 ] Purity: 98% SDS Specification

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Product Details of [ 103438-86-4 ]

CAS No. :	103438-86-4
Formula :	C₇H₅FO₂
M.W :	140.11
SMILES Code :	O=CC1=CC=CC(O)=C1F
MDL No. :	MFCD11110191
Boiling Point :	No data available
InChI Key :	JHPNLGYUKQTWHN-UHFFFAOYSA-N
Pubchem ID :	587789

Safety of [ 103438-86-4 ]

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

Application In Synthesis of [ 103438-86-4 ]

* 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 [ 103438-86-4 ]

[ 103438-86-4 ] Synthesis Path-Downstream 1~35

1
[ 100-39-0 ]
[ 103438-86-4 ]
[ 103438-90-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; water;	3-Hydroxy-2-fluorobenzaldehyde {reported by Kirk et. al., J. Med. Chem. 1986, 29, 1982} (15 g, 107 mmole) was added to an aqueous NaOH solution {(5.14 g, 128 mmole in water (50 mL)} and the mixture was stirred for 5 min to effect complete dissolution. To this was added a solution of benzyl bromide (16.46 g, 96.3 mmole) in methylene chloride (75 mL) followed by tetrabutylammonium iodide (0.5 g, 1.35 mmole) and vigorous stirring was continued overnight. The organic layer was separated and the aqueous layer was extracted with methylene chloride (100 mL). The combined organic layers were washed with 5% aqueous NaOH solution (2×25 mL) followed by water (50 mL) and finally with brine (20 mL). This solution was dried over anhydrous Na2SO4, filtered and evaporated to dryness. The resulting crude light yellow solid was crystallized from cyclohexane (150 mL) to afford the title compound (16.5 g, 75%); mp 88-89 C.
68%	In N-methyl-acetamide; mineral oil;	(i) 2-Fluoro-3-benzyloxybenzaldehyde 2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere. Sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes. Benzyl bromide was added (16.8 ml) and the mixture was stirred overnight. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml). Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the desired product as a yellow solid (18.41 g, 68%): 1H NMR (CD3SOCD3) delta 5.20 (s, 2H), 7.2-7.6 (m, 8H), 10.21(s, 1H)
		(i) 2-Fluoro-3-benzyloxy benzaldehyde 2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere.. sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes.. benzyl bromide was added (16.8 ml) and the mixture was stirred overnight.. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml).. Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo.. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the product as a yellow solid (18.41 g) 1H NMR (DMSO-d6) delta 5.20(s, 2H), 7.2-7.6(m, 8H), 10.21(s, 1H)

References: [1]Patent: US2006/84654,2006,A1 .Location in patent: Page/Page column 123-124.
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.
[3]Patent: US2003/144339,2003,A1 .
[4]Patent: US6737435,2004,B1 .Location in patent: Page/Page column 21.

2
[ 113984-69-3 ]
[ 103438-86-4 ]

References: [1]Synthesis,1988,p. 710 - 712.
[2]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

3
[ 68-12-2 ]
[ 103438-89-7 ]
[ 103438-86-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

4
[ 103438-88-6 ]
[ 103438-86-4 ]

Yield	Reaction Conditions	Operation in experiment
28%	With boron tribromide; In dichloromethane; at -78 - 0℃; for 3h;	Example66; 4-(2-Fluoro-3-hydroxyphenyl)-N-(6-fluoro-lH-indazol-5-yl)-2- methyl-6-oxo-1, 4,5, 6-tetrahydro-3-pyridinecarboxamide;. Step 1;. 2-Fluoro-3-hydroxybenzaldehyde.; BBr3 (4 mL, 4 mmol, 1.0 M in heptane) was added dropwise to a solution of 2- fluoro-5- (methyloxy) benzaldehyde in CH2C12 at-78 C. The reaction mixture was stirred at-78 C for 1 hour, slowly warmed to 0 C and stirred for 2 hours. The reaction mixture was poured into water, extracted with EtOAc (3 x 10 mL). The extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was evaporated, and the residue was purified on silica gel, using 0-20% EtOAc-Hexaxie to give the desired product (158 mg, 28%) as a white solid. MS m/z 141 [M+H] +.
2%		A. 2-Fluoro-3-hydroxybenzaldehyde.; 2-Fluoro-3-methoxybenzaldehyde(1.0 g, 6.49 mmol) was dissolved in CH2Cl2 and cooled to -78 C. Boron tribromide (IM in CH2Cl2, 16.22 mL, 16.22 mmol) was added slowly and the reaction was allowed to warm to rt overnight. An ice/water mixture was added to the resulting slurry and stirred for 30 min. The layers were separated and the organic layer was washed with NaHCO3 (sat.) and 2N NaOH. The aqueous layer was acidified with cone. HCl and extracted with CH2Cl2. The organic layer was dried and concentrated to afford the title compound (0.190 g, 1.36 mmol, 21% yield).
	With boron tribromide; In dichloromethane; at -78 - -20℃; for 4h;	To a solution of the compound 12-1 (1 .4 g, 9 mmol) in 50 mL DCM was added dropwise BBr3 (4M in DCM, 3.6 mL, 13.5 mmol) at -78 C. After the addition, the reaction was stirred at -20 C for 4 hours. After slow addition of ice/water, the layers were separated, the organic layer was washed with water and brine, dried over Na2S04 and evaporated to dryness. The residue was used to next step without further purification.

	With boron tribromide; In dichloromethane; at -70 - -20℃; for 4h;	To a solution of the compound 12-1 (1.4 g, 9 mmol) in 50 mL DCM was added dropwise BBr3 (4M in DCM, 3.6 mL, 13.5 mmol) at -78 C. After the addition, the reaction was stirred at -20 C. for 4 hours. After slow addition of ice/water, the layers were separated, the organic layer was washed with water and brine, dried over Na2SO4 and evaporated to dryness. The residue was used to next step without further purification.
	With boron tribromide; In dichloromethane; at -78 - -20℃; for 4h;	To a solution of the compound 12-1 (1.4 g, 9 mmol) in 50 mL DCM was added dropwise BBr3 (4M in DCM, 3.6 mL, 13.5 mmol) at -78 C. After the addition, the reaction was stirred at -20 C. for 4 hours. After slow addition of ice/water, the layers were separated, the organic layer was washed with water and brine, dried over Na2SO4 and evaporated to dryness. The residue was used to next step without further purification
	With boron tribromide; In dichloromethane; at -70 - -20℃; for 4h;	To a solution of the compound 12-1 (1.4 g, 9 mmol) in 50 mL DCM was added dropwise BBr3 (4M in DCM, 3.6 mL, 13.5 mmol) at -78 C. After the addition, the reaction was stirred at -20 C. for 4 hours. After slow addition of ice/water, the layers were separated, the organic layer was washed with water and brine, dried over Na2SO4 and evaporated to dryness. The residue was used to next step without further purification.

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4584 - 4597.
[3]Patent: WO2005/82890,2005,A1 .Location in patent: Page/Page column 70.
[4]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 115.
[5]Patent: WO2013/61052,2013,A1 .Location in patent: Page/Page column 65.
[6]Patent: US2014/80837,2014,A1 .Location in patent: Paragraph 0167; 0168.
[7]Patent: US2014/234414,2014,A1 .Location in patent: Paragraph 0272; 0273.
[8]Patent: US9139613,2015,B2 .Location in patent: Page/Page column 43.

5
[ 108-24-7 ]
[ 103438-86-4 ]
[ 192927-67-6 ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

6
[ 103438-86-4 ]
[ 960001-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate;	Step A-2-Fluoro-3-(hydroxymethyl)phenol Reduction of <strong>[103438-86-4]2-fluoro-3-hydroxybenzaldehyde</strong> (Kirk, K. L., et. al. J. Med. Chem. 1986, 29, 1982) with sodium borohydride would provide the title compound.
	With sodium tetrahydroborate;	Example 75: (i/-)-3-f Ii -j'2-f iuorQ-3-(4-piperidinyioxy)phbetanyljethyJ}oxv)-5-f 5- (i-methyl-i ^pyrazol^-yi^i MbenzImidazol-i-vn^-thiophenecarboxamideStep A - 2-Fiualpharo-3-(hydroxymethyl)phenolReduction of 2-fiuoro-3-hydrOxybenzaidehyde (Kirk, K. L., et al. J. Med Chem, WBB, 29, 1382) with sodium borohydiide would provide the tiUe compound.

References: [1]Patent: US2008/300247,2008,A1 .Location in patent: Page/Page column 112.
[2]Patent: WO2007/143456,2007,A2 .Location in patent: Page/Page column 243.

7
[ 367-12-4 ]
[ 103438-86-4 ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

8
[ 103438-86-4 ]
5,10,15,20-tetrakis(2-fluoro-3-hydroxyphenyl)porphyrin [ No CAS ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

9
[ 103438-86-4 ]
5,10,15,20-tetrakis(2,4-difluoro-3-hydroxyphenyl)porphyrin [ No CAS ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

10
[ 103438-86-4 ]
Acetic acid 2-fluoro-3-[(1Z,4Z,9Z,15Z)-10,15,20-tris-(3-acetoxy-2-fluoro-phenyl)-porphyrin-5-yl]-phenyl ester [ No CAS ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

11
[ 103438-86-4 ]
Acetic acid 3-[(1Z,4Z,9Z,15Z)-10,15-bis-(3-acetoxy-2,4-difluoro-phenyl)-20-(3-acetoxy-2,5-difluoro-phenyl)-porphyrin-5-yl]-2,6-difluoro-phenyl ester [ No CAS ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

12
[ 103438-89-7 ]
[ 103438-86-4 ]

References: [1]South African Journal of Chemistry,1997,vol. 50,p. 40 - 47.

13
[ 103438-86-4 ]
[ 103438-94-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

14
[ 103438-86-4 ]
[ 103438-97-7 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

15
[ 103438-86-4 ]
[ 103439-01-6 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

16
[ 103438-87-5 ]
[ 103438-86-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

17
3-methoxy-2-nitrobenzaldehyde dimethyl acetal [ No CAS ]
[ 103438-86-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1982 - 1988.

18
[ 2033-24-1 ]
[ 864083-06-7 ]
[ 103438-86-4 ]
4-(2-fluoro-3-hydroxyphenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With ammonium acetate; acetic acid; at 120℃; for 3h;	Step 2;. 4-(2-Fluoro-3-hydroxyphenyl)-N-(6-fluoro-lH-indazol-5-yl)-2-methyl-6- oxo-1, 4, 5, 6-tetrahydro-3-pyridinecarboxamide;. The product of Step 1 (0.060 g, 0.43 mmol, 1.0 equiv), the product of Example 63, Step 1 (0.10 g, 0.43 mmol, 1.0 equiv), 2, 2-dimethyl-1, 3-dioxane-4,6-dione (62 mg, 0.43 mmol, 1.0 equiv), and ammonium acetate (35 mg, 0.45 mmol, 1.05 equiv) were dissolved in acetic acid (0.5 mL) and heated at 120 C for 3 hours. Addition of water to the stirred reaction mixture induced precipitation of a solid residue. The solid was recovered by filtration and the residue was partitioned between EtOAc and satd. NaHC03. The phases were separated and the organic layer was washed with satd. NaCl, dried over Na2S04, filtered and concentrated en vacuo. The residue was purified by reverse phase HPLC (Xterra Prep 30x100, 25 mL/min, 10-40% CH3CN-H20- 0. 1% TFA, over 12 minutes) to provide product (35 mg, 20%) as a white solid. MS (ES+) m/z 399 [M+H] +.

References: [1]Patent: WO2005/82890,2005,A1 .Location in patent: Page/Page column 71.

19
[ 1132074-10-2 ]
[ 103438-86-4 ]
[ 1132074-77-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 19 3-[({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)methyl]-2-fluorophenol 4-{2-[4-(2-Amino-ethyl)-phenoxy]-ethyl}-2-((1R)-3-diisopropylamino-1-phenyl-propyl)-phenol (Product of preparation 4, 40 mg, 0.084 mmol) was dissolved in dichloromethane (5 ml) and acetic acid (in excess of 0.005 ml) followed by the addition of 2-Fluoro-3-hydroxy-benzaldehyde (11.8 mg, 0.0843 mmol) and magnesium sulphate which was stirred under nitrogen at room temperature for 30 mins. Sodium borohydride was then added (6.38 mg, 0.169 mmol) and the reaction was stirred overnight under nitrogen at room temperature. The reaction was diluted with saturated sodium hydrogen carbonate solution (5 ml) and poured through a phase separation cartridge. The organic layer was evaporated in vacuo and the crude material was purified by HPLC method B to afford the title compound. LCMS Method B (acidic conditions) RT 2.2 min (100% area) ES m/z 599 [M+H]+

References: [1]Patent: US2009/76152,2009,A1 .Location in patent: Page/Page column 23.

20
[ 743460-14-2 ]
[ 103438-86-4 ]
[ 1205551-65-0 ]

Yield	Reaction Conditions	Operation in experiment
47%		Example 2 Biphenyl-2-yl-carbamic acid 1-[9-(2-fluoro-3-hydroxy-benzylamino)-nonyl]-piperidin-4-yl ester To a solution of biphenyl-2-yl-carbamic acid 1-(9-amino-nonyl)-piperidin-4-yl ester (Preparation 2, 150 mg, 343 mumol) in ethanol (5 ml) were added <strong>[103438-86-4]2-fluoro-3-hydroxybenzaldehyde</strong> (Synthesis, (9), 710-12, 1988; 48.1 mg, 343 mumol), acetic acid (in excess of 0.02 ml, 343 mumol) and sodium sulfate (drying agent), and the mixture was stirred under nitrogen at room temperature for 1 hour. Sodium triacetoxyborohydride was then added (145 mg, 686 mumol) and the mixture stirred under nitrogen at room temperature for 24 hours. The mixture was diluted with water (2 ml), the solvent removed in vacuo and the residue partitioned between saturated sodium hydrogen carbonate solution (10 ml) and dichloromethane (10 ml). The organic layer was separated, washed with brine (5 ml), dried (sodium sulphate) and the solvent removed in vacuo to yield a colourless gum. The residue was purified using a RediSep silica gel cartridge eluding with dichloromethane:methanol:0.88 ammonia (99:1:0.1 to 95:5:0.5, by volume) to afford the title compound as a colourless gum, 47% yield, 90 mg. 1H NMR (400 MHz, METHANOL-d4) delta=1.27-1.36 (m, 10H), 1.45-1.56 (m, 4H), 1.56-1.66 (m, 2H), 1.81-1.89 (m, 2H), 2.23-2.35 (m, 4H), 2.58-2.71 (m, 4H), 3.80 (s, 2H) 4.56-4.63 (m, 1H), 6.75-6.78 (td, 1H), 6.80-6.85 (td, 1H), 6.91-6.95 (td, 1H), 7.23-7.44 (m, 8H), 7.52-7.56 (m, 1H) ppm. LRMS: m/z 562 [M+H]+, 560 M-

References: [1]Patent: US2010/16366,2010,A1 .Location in patent: Page/Page column 16.

21
[ 14527-26-5 ]
[ 103438-86-4 ]
[ 105-56-6 ]
C₁₂H₈FN₃O₂S [ No CAS ]