133357-62-7|Methyl 3-(bromomethyl)-5-methoxybenzoate| Ambeed

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Quality Control of [ 133357-62-7 ] Purity: 98% SDS Specification

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Product Details of [ 133357-62-7 ]

CAS No. :	133357-62-7
Formula :	C₁₀H₁₁BrO₃
M.W :	259.10
SMILES Code :	O=C(OC)C1=CC(OC)=CC(CBr)=C1
MDL No. :	MFCD03265289
InChI Key :	SZSHGWWDWSLOQS-UHFFFAOYSA-N
Pubchem ID :	14846395

Safety of [ 133357-62-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Application In Synthesis of [ 133357-62-7 ]

* 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 [ 133357-62-7 ]

[ 133357-62-7 ] Synthesis Path-Downstream 1~20

1
[ 108593-44-8 ]
[ 133357-62-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

2
[ 15681-48-8 ]
[ 133357-62-7 ]
[ 133344-03-3 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

3
[ 133357-62-7 ]
[ 1001419-88-0 ]

Yield	Reaction Conditions	Operation in experiment
90%		A suspension of NaH (70 mg of a 60% suspension in oil, 1.750 mmol) in THF (3 mL) was stirred at 0 C. under N2 (g) for 15 min. The reaction was cooled to -30 C. and oxazolidin-2-one (125 mg, 1.436 mmol) was added. The mixture was stirred at -30 C. for 30 min, then was warmed to RT and stirred for 30 min. The mixture was cooled to -30 C. again and a solution of <strong>[133357-62-7]methyl 3-(bromomethyl)-5-methoxybenzoate</strong> (200 mg, 0.772 mmol) in THF (2 mL) was added. The mixture was stirred at RT for 5 days, then was cooled to -30 C. and sat. aqueous NH4Cl (1 mL) was added. The aqueous layer was back-extracted with EtOAc (2×5mL), and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed [SiO2; EtOAc/Hexane (1:1)] to give Part A compound 184 mg, 90% yield) as a clear oil. [M+H]+=266.01; 1H NMR (500 MHz, CDCl3) delta 3.46 (t, J=7.70 Hz, 2 H) 3.85 (s, 3 H) 3.92 (s, 3 H) 4.33 (t, J=7.70 Hz, 2 H) 4.44 (s, 2 H) 7.05 (s, 1 H) 7.50 (s, 1 H) 7.54 (s, 1 H).

References: [1]Patent: US2008/9465,2008,A1 .Location in patent: Page/Page column 76.

4
[ 133357-62-7 ]
[ 133344-04-4 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

5
[ 133357-62-7 ]
[ 133344-05-5 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

6
[ 133357-62-7 ]
[ 133344-07-7 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

7
[ 133357-62-7 ]
[ 114862-75-8 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6313 - 6316.

8
[ 133357-62-7 ]
[ 109-85-3 ]
[ 900157-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 20℃;	Intermediate 102.5; A mixture of 3-Bromomethyl-5-methoxy-benzoic acid methyl ester (300 mg, 1.16 mmol) (see e.g. Tetrahedron Lett, 1993, 31, 6313) , 2-Methoxy-ethylamine (260 mg, 3.47 mmol) and K2CO3 (0.32 g, 2.32 mmol) in CH3CN (5 mL) are stirred at RT. for over night. After adding H2O (20 mL), the reaction mixure is extracted with CH2CI2 (20 mL, 2x). The combined organic phases are washed with H2O, brine and dried (Na2SO4), concentrated under reduced EPO <DP n="155"/>to give 3-Methoxy-5-[(2-methoxy-ethylamino)-methyl]-benzoic acid methyl ester as an oil (217 mg, 0.85 mmol; 85%; ES-MS: M+H = 254 ; HPLC: tRtheta, = 2.29 minutes). This crude material is used without purification. To a mixture of this crude material and Et3N (0.48 ml, 3.47 mmol), (BOC)2O (380 mg, 1.74 mmol) in DCM (5 mL) is added at RT. After stirring for 1 h, the reaction mixture is quenched by adding H2O, and mixture is extracted with DCM. The combined organic phases are washed with H2O, brine and dried (MgSO4), concentrated under reduced pressure and silica gel flash chromatography to give Intermediate 102.5 as white amorphous; Rf = 0.47 (AcOEt:n-Hex=1:2) 1H NMR (400 MHz, CDCI3); J1.40-1.55 (brs, 9H), 3.30 (s, 3H), 3.35-3.55 (m, 4H), 3.80 (s, 3H), 3.90 (s, 3H), 4.45 (brs, 2H), 6.95-7.0 (brs, 1H), 7.40 (m, 1H), 7.50 (m, 1H).

References: [1]Patent: WO2006/74924,2006,A1 .Location in patent: Page/Page column 153-154.

10
[ 133357-62-7 ]
[ 147621-18-9 ]
[ 1352723-65-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7220 - 7231.

11
[ 133357-62-7 ]
[ 147621-18-9 ]
[ 1322716-81-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7220 - 7231.

12
[ 20319-44-2 ]
[ 133357-62-7 ]

References: [1]Patent: US2014/18368,2014,A1 .

13
[ 367519-84-4 ]
[ 133357-62-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With phosphorus tribromide; In dichloromethane; at 20℃; for 1h;	Step 14b. Methyl 3-(bromomethyl)-5-methoxybenzoate (compound 1203) To a stirred solution of compound 1202 (800 mg, 4.0 mmol) in dichloromethane (10 mL) was added PBr3 (0.4 mL, 4.3 mmol). The reaction mixture was stirred for 1 h at room temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic phase was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography eluted with hexanes/ethyl acetate (5:1) to obtain compound 1203 as a yellow oil. (640 mg, 61% yield). 1H NMR (400 MHz, CDCl3): delta 3.85 (s, 3H), 3.92 (s, 3H), 7.12 (br, 1H), 7.49 (br, 1H), 7.65 (br, 1H).

References: [1]Patent: US2014/18368,2014,A1 .Location in patent: Paragraph 0162; 0250.

14
[ 133357-62-7 ]
[ 1552310-74-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium azide; In N,N-dimethyl-formamide; at 20℃; for 2h;	Step 14c. Methyl 3-(azidomethyl)-5-methoxybenzoate (compound 1204) To a stirred solution of compound 1203 (640 mg, 2.5 mmol) in DMF (5 mL) was added NaN3 (1.1 g 16.9 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction solution was diluted with ethyl acetate and washed with water and brine. The organic phase was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography eluted with hexanes/ethyl acetate (5:1) to afford compound 1204 as a yellow oil (500 mg, 91% yield). LCMS: m/z 263.2 [M+1+41]+.

References: [1]Patent: US2014/18368,2014,A1 .Location in patent: Paragraph 0162; 0251.

15
[ 133357-62-7 ]
[ 1393565-75-7 ]

References: [1]Patent: US2014/18368,2014,A1 .

16
[ 133357-62-7 ]
[ 1552310-76-5 ]

References: [1]Patent: US2014/18368,2014,A1 .

17
[ 133357-62-7 ]
[ 1552310-77-6 ]

References: [1]Patent: US2014/18368,2014,A1 .

18
[ 133357-62-7 ]
[ 1552310-80-1 ]

References: [1]Patent: US2014/18368,2014,A1 .

19
[ 133357-62-7 ]
[ 1552310-81-2 ]

References: [1]Patent: US2014/18368,2014,A1 .

20
[ 133357-62-7 ]
[ 74-89-5 ]
[ 1552310-79-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With methanol; In water; N,N-dimethyl-formamide; at 20℃; for 0.166667h;	Step 15a. Methyl 3-methoxy-5-((methylamino)methyl)benzoate (compound 1301) To a solution of 1203 (150 mg, 0.6 mmol) in DMF (3 mL) was added methylamine methanol solution (2.5 mL). The reaction mixture was stirred at room temperature for 10 min. Water (10 mL) was added to the reaction mixture and the resulting reaction mixture was extracted with ethyl acetate (10 mL*2). The combined organic layers were washed with water. The organic phase was dried over Na2SO4, filtered and evaporated to give product 1301 as light yellow oil (100 mg, 83%). LCMS: m/z 210.1 [M+1]+. 1H NMR (400 MHz, CDCl3): delta 2.45 (s, 3H), 3.77 (s, 2H), 3.85 (s, 3H), 3.92 (s, 3H), 7.10 (s, 1H), 7.45 (s, 1H), 7.59 (s, 1H).

References: [1]Patent: US2014/18368,2014,A1 .Location in patent: Paragraph 0162; 0257.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reactions of Ethers • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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Code	Phrase
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P401
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Code	Phrase
H200	Unstable explosive
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Code	Phrase
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H302	Harmful if swallowed
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H311	Toxic in contact with skin
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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.: 133357-62-7

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CAS No.: 133357-62-7

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Product Details of [ 133357-62-7 ]

Safety of [ 133357-62-7 ]

Application In Synthesis of [ 133357-62-7 ]

[ 133357-62-7 ] Synthesis Path-Downstream 1~20

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