33172-56-4|5-Bromo-2-hydroxy-3-methylbenzaldehyde| Ambeed

CAS No. :	33172-56-4
Formula :	C₈H₇BrO₂
M.W :	215.04
SMILES Code :	O=CC1=CC(Br)=CC(C)=C1O
MDL No. :	MFCD01040324
InChI Key :	PZGFSVYPDAQKHJ-UHFFFAOYSA-N
Pubchem ID :	2757016

Safety of [ 33172-56-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 33172-56-4 ]

* 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 [ 33172-56-4 ]

[ 33172-56-4 ] Synthesis Path-Downstream 1~54

2
2-oxy-m-toluylaldehyde [ No CAS ]
[ 33172-56-4 ]

References: [1]Chemische Berichte,1901,vol. 34,p. 2102.

3
sodium salt of/the/ 4-oxy-5-methyl-3-formyl-azobenzene-sulfonic acid-(4') [ No CAS ]
[ 33172-56-4 ]

References: [1]Chemische Berichte,1901,vol. 34,p. 2102.

4
[ 824-42-0 ]
[ 33172-56-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bromine; acetic acid; at 0℃; for 2h;	The compound BB-8-1 (5g, 36.72mmol) was dissolved in acetic acid (30mL), cooled to 0 , then added dropwise liquid bromine(6.75g, 42.23mmol), which was allowed to react at 0 2 hours.After completion of the reaction, water was added (100 mL), filtered, solid waswashed with water, and dried to give the title compound BB-8-2 (yellow solid, 7.5g, yield: 95%)
89%	With bromine; acetic acid; at 20℃; for 2h;Cooling with ice;	Under an ice bath, bromine (4.6 g, 28.75 mmol) was added to a solution of 2-hydroxy-3-methylbenzaldehyde (3.4 g, 25.0 mmol) in glacial acetic acid (20 mL), and the reaction solution was stirred at room temperature for 2 h. Water (100 mL) was added to the reaction solution, and the precipitated solid was filtered out. The filter cake was washed with water (100 mL) and dried under vacuum to give 5-bromo-2-hydroxy-3-methylbenzaldehyde (4.8 g, 89%) in the form of a yellow solid, which was directly used in the next step. LCMS (ESI) [M+H]+=216.9; 1H NMR (400 MHz, CDCl3) δ 11.19 (s, 1H), 9.82 (s, 1H), 7.66-7.46 (m, 2H), 2.26 (s, 3H).
88.6%	With bromine; In acetic acid; at 0℃; for 2h;	[1050] The solution of 2-Hydroxy-3-methylbenzaldehyde (1.0 g, 7.35 mmole) in acetic acid (6 mL) was cooled to 0 C (ice bath). Bromine (1.36 g, 8.52 mmole) was added dropwise and allowed to stir for 2 hours. The reaction was warmed to room temperature and diluted with water (100 mL) yielding a light orange precipitate. The solid was filtered and washed with water (10 mL). Dried on high vacuum to give a light brown solid (1.4 g, 88. 6%). 1H NMR (CDC13/400 MHz) 11.16 (s, 1H), 9.79 (s, 1H), 7.48 (s, 1H), 7.46 (s, 1H), 2.23 (s, 3H).

References: [1]Journal of Catalysis,2004,vol. 221,p. 77 - 84.
[2]Patent: CN105732602,2016,A .Location in patent: Paragraph 0175; 0177; 0178; 0179; 0180.
[3]Patent: US2020/369676,2020,A1 .Location in patent: Paragraph 0842-0843.
[4]Patent: WO2004/87686,2004,A2 .Location in patent: Page 507-508.
[5]Tetrahedron Letters,2003,vol. 44,p. 6813 - 6816.
[6]Organic Letters,2014,vol. 16,p. 4150 - 4153.

5
[ 33172-56-4 ]
[ 2156-04-9 ]
[ 617708-32-4 ]

References: [1]Journal of Catalysis,2004,vol. 221,p. 77 - 84.
[2]Tetrahedron Letters,2003,vol. 44,p. 6813 - 6816.

6
[ 866951-46-4 ]
[ 33172-56-4 ]
[ 1000415-03-1 ]

References: [1]Russian Chemical Bulletin,2006,vol. 55,p. 1794 - 1802.

7
[ 71103-46-3 ]
[ 33172-56-4 ]
[ 1000415-02-0 ]

References: [1]Russian Chemical Bulletin,2006,vol. 55,p. 1794 - 1802.

8
[ 1000414-90-3 ]
[ 33172-56-4 ]
[ 1000414-98-1 ]

References: [1]Russian Chemical Bulletin,2006,vol. 55,p. 1794 - 1802.

9
[ 33172-56-4 ]
N-(3-methylsalicylidene)-N'-(4-vinylphenyl-3-methylsalicylidene)ethylenediimine [ No CAS ]

References: [1]Journal of Catalysis,2004,vol. 221,p. 77 - 84.
[2]Tetrahedron Letters,2003,vol. 44,p. 6813 - 6816.

10
[ 33172-56-4 ]
N,N'-bis-(3-methylsalicylidene)-1,2-ethylenediamine [ No CAS ]

References: [1]Journal of Catalysis,2004,vol. 221,p. 77 - 84.

11
[ 33172-56-4 ]
C₃₄H₃₂N₂O₂ [ No CAS ]

References: [1]Journal of Catalysis,2004,vol. 221,p. 77 - 84.

12
[ 25597-16-4 ]
[ 33172-56-4 ]
ethyl 6-bromo-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; triethylamine; In dimethyl sulfoxide; at 90℃; for 18h;	[1051] A mixture of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (1.40 g, 6.51 mmole), K2C03 (1. 80 G, 13.02 mmole), triethylamine (2.63 g, 26.05 mmole), and ethyl 4,4, 4- trifluorocrotonate (4.38 g, 26.05 mmole) in anhydrous DMSO (5.0 mL) was heated to 90 C under a dry N2 atmosphere for 18 hrs. The contents were poured into 2.4 N HCL (50 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give a dark yellow oil which was subject to flash chromatography (silica gel) and eluted with 10% EtOAc in hexanes to give a yellow solid (1.6 g, 68%). GCMS 7N/Z 364.0 (M+). H NMR (CDC13/400 MHz) 7.59 (s, 1H), 7.27 (s, 1H), 7.16 (s, 1H), 5.70 (q, 1H, J=7. 0 Hz), 4.29 (m, 2H), 2.19 (s, 3H), 1.32 (m, 3H).

References: [1]Patent: WO2004/87686,2004,A2 .Location in patent: Page 508.
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.

13
[ 33172-56-4 ]
[ 6018-89-9 ]
[ 75-31-0 ]
[ 165620-53-1 ]

References: [1]Inorganic Chemistry,1995,vol. 34,p. 4032 - 4040.
Inorg. Chem.,.

14
[ 33172-56-4 ]
[ 6018-89-9 ]
[ 75-04-7 ]
[ 165620-52-0 ]

References: [1]Inorganic Chemistry,1995,vol. 34,p. 4032 - 4040.
Inorg. Chem.,.

15
[ 50-00-0 ]
[ 2362-12-1 ]
[ 33172-56-4 ]

Yield	Reaction Conditions	Operation in experiment
36.9%		(2) Preparation of the intermediate 83(2).; Triethylamine (2.5 ml, 17.94 mmol) was added to a mixture of paraformaldehyde (811 mg, 27.00 mmol), magnesium chloride (1.714 g, 18.00 mmol) and tetrahydrofuran (45 ml), and the mixture was stirred at room temperature for 20 minutes. The intermediate 83(1) (1.683 g, 9.00 mmol) was added to the reaction mixture, and the mixture was refluxed for 8 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with n-hexane to give the title compound (714 mg, 36.9 %) as a yellowish-orange solid. 1H-NMR (CDCl3) δ: 2.26 (3H, s), 7.49-7.52 (2H, m), 9.82 (1H, s), 11.19 (1H, s).

References: [1]Patent: EP2272817,2011,A1 .Location in patent: Page/Page column 271.

16
[ 14804-31-0 ]
[ 33172-56-4 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.
[2]Patent: EP2272817,2011,A1 .

17
[ 33172-56-4 ]
[ 5548-30-1 ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

18
[ 33172-56-4 ]
2,5-dimethoxy-3-methyl-6-nitro-benzaldehyde [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

19
[ 33172-56-4 ]
C₁₀H₁₃NO₃ [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

20
[ 33172-56-4 ]
2-azido-3,6-dimethoxy-5-methylbenzaldehyd [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

21
[ 33172-56-4 ]
2,2'-[(2-azido-3,6-dimethoxy-5-methylphenyl)methanediyl]bis(5-methylfuran) [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

22
[ 33172-56-4 ]
[ 124-41-4 ]
[ 886503-93-1 ]

References: [1]Organic Letters,2014,vol. 16,p. 4150 - 4153.

23
[ 100-97-0 ]
[ 2362-12-1 ]
[ 33172-56-4 ]

References: [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 639 - 645.
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.

24
[ 95-48-7 ]
[ 33172-56-4 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 639 - 645.

25
[ 578-58-5 ]
[ 33172-56-4 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.

26
[ 33172-56-4 ]
6-bromo-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1162 - 1166.

27
[ 33172-56-4 ]
[ 96628-67-0 ]
tert-butyl (2-(4-bromo-2-formyl-6-methylphenoxy)ethyl)carbamate [ No CAS ]