4-Bromo-3-fluorobenzaldehyde | Benzene Compounds

CAS No. :	133059-43-5
Formula :	C₇H₄BrFO
M.W :	203.01
SMILES Code :	BrC1=C(C=C(C=O)C=C1)F
MDL No. :	MFCD03095000
InChI Key :	SWHUROFMIMHWKS-UHFFFAOYSA-N
Pubchem ID :	2783411

Safety of 4-Bromo-3-fluorobenzaldehyde

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of 4-Bromo-3-fluorobenzaldehyde

* 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 [ 133059-43-5 ]

[ 133059-43-5 ] Synthesis Path-Downstream 1~7

1
4-bromo-3-fluorobenzyl acetate [ No CAS ]
[ 133059-43-5 ]
[ 222978-01-0 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: Preparation of (4-bromo-3-fluorophenyl) methanol; To a room temperature solution of 1-bromo-4- (bromomethyl)-2-fluorobenzene from Step 1 (11. 8 g) in DMF (150 mL) was added sodium acetate (10.8 g). The mixture was heated at 80 C for 16 hours. It was cooled to room temperature and poured into ice and saturated aqueous sodium bicarbonate (200 mL), and extracted with diethyl ether (2 X 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The crude material was purified by chromatography on Si02 using ethyl acetate and hexanes (1: 25 to 1 : 10) to yield 4-bromo-3- fluorobenzyl acetate (containing about 15% of 4-bromo-3-fluorobenzaldehyde). The residue was dissolved in methanol (100 mL), cooled at 0 C and sodium methoxide (250 mg) was added. The reaction mixture was stirred at room temperature for 2 hours. It was cooled to 0 C and sodium borohydride was added (1.5 g). Stirred at 0 C for 1 hour and poured into ice and saturated aqueous ammonium chloride (200 mL). Extracted with ethyl acetate (2 X 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by chromatography on Si02 using ethyl acetate and hexanes (1: 5 to 1: 3) to yield the title compound. lH NMR (CD3COCD3) o 7.55-7. 65 (1H, m), 7.28 (1H, d), 7.15 (1H, d), 4.63 (2H, d), 4.50 (1H, t).
		Step 4: Preparation of (4-bromo-3-fluorophenyl)methanol; To a room temperature solution of l-bromo-4-(bromomethyl)-2-fluorobenzene from Step 3 (1 1.8 g) in DMF (150 mL) was added sodium acetate (10.8 g). The mixture was heated at 80C for 16 hours. It was cooled to room temperature and poured into ice and saturated aqueous sodium bicarbonate (200 mL), and extracted with diethyl ether (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The crude material was purified by cliromatography on SiO2 using ethyl acetate and hexanes (1:25 to 1: 10) to yield 4-bromo-3- fluorobenzyl acetate (containing about 15% of 4-bromo-3-fluorobenzaldehyde). The residue was dissolved in methanol (100 mL), cooled to 00C and sodium methoxide (250 mg) was added. The reaction mixture was stirred at room temperature for 2 hours. It was cooled to 00C and sodium borohydride was added (1.5 g). The mixture was stirred at 00C for 1 hour and poured into ice and saturated aqueous ammonium chloride (200 mL). The mixture was extracted with ethyl acetate (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes (1:5 to 1:3) to yield the title compound. EPO <DP n="31"/>1H NMR (CD3COCD3) delta 7.55-7.65 (1 H, m), 7.28 (1 H, d), 7.15 (1 H, d), 4.63 (2 H, d), 4.50 (1 H, t).

References: [1]Patent: WO2005/56529,2005,A1 .Location in patent: Page/Page column 36-37.
[2]Patent: WO2006/133559,2006,A1 .Location in patent: Page/Page column 29.

2
[ 222978-01-0 ]
[ 133059-43-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With manganese(IV) oxide; In chloroform; at 20℃;	To a solution of <strong>[222978-01-0](4-bromo-3-fluoro-phenyl)-methanol</strong> (4.3 g, 21 mmol) in CHCl3 (50 mL) was added manganese dioxide (18.7 g, 210 mmol), and the resulting mixture was stirred overnight at room temperature until the starting material had been consumed. After filtration, the filtrate was concentrated in vacuo to give product (2.3 g, 55%).
	With N-chloro-succinimide; cyfluthrin; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; In dichloromethane;	Step A Preparation of 4-Bromo-3-fluorobenzaldehyde To a well-stirred mixture of <strong>[222978-01-0]4-bromo-3-fluorobenzyl alcohol</strong> (as described in Example 9, Step B) (10.25 g, 0.05 mol), TEMPO (0.781 g, 0.005 mol) and tetrabutylammonium fluoride (1.39 g, 0.005 mol) in CH2Cl2 (200 mL) and a solution of 0.5M NaHCO3/0.05M K2CO3 (200 mL) was added N-chlorosuccinimide (9.35 g, 0.07 mol). After 6 hrs, the layers were separated, the aqueous layer back-washed with CH2Cl2 (2*50 mL), the organics combined and dried (Na2SO4). The solution was filtered, concentrated to half its volume, then chromatographed (silica gel, CH2Cl2) to give the title compound. 1H NMR (CDCl3) delta 9.96 (s, 1H), 7.78 (dd, 1H, J=2, 8 Hz), 7.62 (dd, 1H, J=2, 8 Hz), 7.56 (dd, 1H, J=2, 8 Hz).

References: [1]Patent: US2010/216806,2010,A1 .Location in patent: Page/Page column 103.
[2]Patent: US6297239,2001,B1 .

3
NaHCO₂ [ No CAS ]
[ 222978-01-0 ]
[ 133059-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; cyfluthrin; tetrabutyl ammonium fluoride; potassium carbonate; In dichloromethane;	Step A Preparation of 4-Bromo-3-fluorobenzaldehyde To a well-stirred mixture of <strong>[222978-01-0]4-bromo-3-fluorobenzyl alcohol</strong> (as described in Example 1, Step B) (10.25 g, 0.05 mol), TEMPO (0.781 g, 0.005 mol) and tetrabutylammonium fluoride (1.39 g, 0.005 mol) in CH2Cl2 (200 mL) and a solution of 0.5M NaHCO2/0.05M K2CO3(200 mL) was added N-chlorosuccinimide (9.35 g, 0.07 mol). After 6 hrs, the layers were separated, the aqueous layer back-washed with CH2Cl2 (2*50 mL), the organics combined and dried (Na2SO4). The solution was filtered, concentrated to half its volume, then chromatographed (silica gel, CH2Cl2) to give the title compound. 1H NMR (CDCl3) delta 9.96 (s, 1H), 7.78 (dd, 1H, J=2, 8 Hz), 7.62 (dd, 1H, J=2, 8 Hz), 7.56 (dd, 1H, J=2, 8 Hz).

References: [1]Patent: US6284755,2001,B1 .

4
[ 133059-43-5 ]
[ 222978-01-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With methanol; sodium tetrahydroborate; at 20℃; for 2h;	4-Bromo-3-fluorobenzaldehyde (500mg, 2.46mmol) was dissolved in methanol (10mL), followed by addition of sodium borohydride (465.9mg, 12.31mmol). The mixture was stirred at room temperature for 2 hours, then evaporated under reduced pressure. The residue was diluted with ethyl acetate (50mL), washed with saturated brine (20mL) and water (20mL). The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give compound 21-d (501mg, yield 99%), which was directly used in the next step without further purification. 1H NMR (400 MHz, CDCl3) delta: 7.54-7.50 (m, 1H), 7.17-7.12 (m, 1H), 7.03-7.01 (m, 1H), 4.67 (s, 2H), 1.90 (br, 1H) ppm.
97%		Step i :Solid NaBH4 (603 mg, 15.9 mmol) is added to a solution of ketone 50a (4.11 g, 19.92 mmol) dissolved in MeOH (62 mL) at O0C. The reaction is warmed to RT and is allowed to stir for 2 h. The reaction is quenched with aqueous HCI (1 N, 20 mL), the MeOH is removed by concentration and the product extracted with EtOAc (2 x 50 <n="111"/>mL). The organic layer is washed with brine (50 ml_), dried over MgSO4, filtered and concentrated to afford alcohol 50b (4.1 g, 97% yield). This material is used as is in the next step.
97%	With sodium tetrahydroborate; In methanol; at 0 - 25℃; for 2h;	Solid NaBH4 (603 mg, 15.9 mmol) is added to a solution of aldehyde 48a (4.1 1 g,19.92 mmol) dissolved in MeOH (62 mL) at O0C. The reaction is warmed to RT and is allowed to stir for 2 h. The reaction is quenched with aqueous HCI (1 N, 20 mL), the MeOH is removed by concentration and the product extracted with EtOAc (2 x 50 mL). The organic layer is washed with brine (50 mL), dried over MgSO4, filtered and concentrated to afford alcohol 48b (4 1 g, 97% yield). This material is used as is in the next step.

97%	With methanol; sodium tetrahydroborate; In tetrahydrofuran;	To a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBH4 (3.73 g, 99 mmol) in THF (100 mL) was added MeOH (100 mL) dropwise at 20 C. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in DCM (200 mL) and washed with H2O (60 mL) and brine (60 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a white solid of (4-bromo-3-fluorophenyl)methanol (9.8 g, 47.7 mmol, 97.0% yield): 1H NMR (400 MHz, CD3OD) delta 7.54 (t, J=7.8 Hz, 1H), 7.18 (d, J=9.6 Hz, 1H), 7.06 (d, J=7.2 Hz, 1H), 4.56 (s, 2H); ES-LCMS m/z 188.9 (M-17).
97%	With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20℃;	To a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBH4 (3.73 g, 99 mmol) in THF (100 mL) was added MeOH (100 inL) dropwise at 20 C. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in DCM (200 mL) and washed with H20 (60 mL) and brine (60 mL). The organic layer was dried over Na2S04, filtered and concentrated to yield a white solid of (4-bromo-3- fluorophenyl)methanol (9.8 g, 47.7 mmol, 97.0% yield): lH NMR (400 MHz, CD3OD) delta 7.54 (t, J = 7.8 Hz, 1H), 7.18 (d, J = 9.6 Hz, 1H), 7.06 (d, J = 7.2 Hz, 1H), 4.56 (s, 2H); ES-LCMS m/z 188.9 (M-17).
	With methanol; sodium tetrahydroborate; at 20℃; for 2h;	To a solution of 4-bromo-3-fluoro-benzaldehyde (10.1 g, 49.8 mmol, 1.0 eq) in MeOH (100 mL) was added NaB (3.8 g, 99.6 mmol, 2.0 eq). The mixture was stirred at rt for 2 h. The reaction mixture was extracted with ethyl acetate, washed with brine and water. The organic layer was dried over Na2S04 and evaporated to give the crude product (4-bromo-3-fluoro-ph -methanol (10.3 g, 100%).
	With methanol; sodium tetrahydroborate; at 0℃; for 3h;	To a solution of 4-bromo-3-fluoro- benzaldehyde (20 g, 99.5 mmol) in MeOH (200 mL) at 0 C was added NaBH4 (5.7g, 150 mmol) portion wise, and the reaction was stirred for 3 h. Then the mixture was quenched with water, and extracted with EtOAc three times. The combined organic layers were concentrated to afford crude compound A26- 1, which was used in the next step without purification.

References: [1]Patent: EP3483142,2019,A1 .Location in patent: Paragraph 0221; 0224.
[2]Patent: WO2009/62285,2009,A1 .Location in patent: Page/Page column 109-110.
[3]Patent: WO2009/62288,2009,A1 .Location in patent: Page/Page column 112.
[4]Patent: US2014/275111,2014,A1 .Location in patent: Paragraph 0343; 0344.
[5]Patent: WO2014/141187,2014,A1 .Location in patent: Page/Page column 75.
[6]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 297.
[7]Patent: WO2015/176267,2015,A1 .Location in patent: Page/Page column 133.

5
[ 2612-28-4 ]
[ 133059-43-5 ]
2-(4-bromo-3-fluorophenyl)-5-propyl-1,3-dioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31 g	With toluene-4-sulfonic acid; In toluene; for 4h;Inert atmosphere; Reflux; Dean-Stark;	(2-1) In a nitrogen atmosphere, 4-bromo-3-fluorobenzalde- hyde (20.0 g), 2-propyl-1 ,3-propanediol (11.6 g), and p-toluenesulfonic acid monohydrate (0.9 g) were dissolved in toluene (100 mE), and the resulting solution was stirred for four hours under solvent refluxing while removing generated water with a Dean-Stark apparatus. Afier the mixture was left to cool, a saturated aqueous sodium hydrogen carbonate solution (100 mE) was added thereto to conduct separation, and the organic layer was washed with saturated saline (100 mE) and dried by addition of anhydrous sodium sulfate. Afier the solvent was distilled away at a reduced pressure, the residue was purified by silica gel colunm chromatography. As a result, crude 2-(4-bromo-3-fluorophenyl)-5-propyl- 1 ,3-di- oxane (31.0 g) was obtained.
	With toluene-4-sulfonic acid; In toluene; for 4h;Dean-Stark; Reflux; Inert atmosphere;	(2-1) under a nitrogen atmosphere, 4-bromo-3-fluorobenzaldehyde (20.0g), 2- propyl-1,3-propanediol (11.6g) and p-toluenesulfonic acid monohydrate (0.9g ) was dissolved in toluene (100mL), while using the Dean-Stark apparatus at reflux of the solvent while removing the formed water was stirred for 4 hours. After cooling, saturated aqueous sodium bicarbonate solution (100 mL) were separated, washed with saturated brine (100 mL) and the organic layer was washed, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography was purified to give crude 2- (4-bromo-3-fluorophenyl) -5-propyl-1,3-dioxane (31.0g) .

References: [1]Patent: US2016/159765,2016,A1 .Location in patent: Page/Page column 0158.
[2]Patent: CN105358538,2016,A .Location in patent: Paragraph 0302; 0304; 0305.

6
[ 2612-28-4 ]
[ 133059-43-5 ]
trans-2-[4-(4-(3,4,5-trifluorobenzyloxy)-3,5-difluorophenyl)-3-fluorophenyl]-5-propyl-1,3-dioxane [ No CAS ]

References: [1]Patent: US2016/159765,2016,A1 .

7
[ 2612-28-4 ]
[ 133059-43-5 ]
trans-2-[4-(4-(3,4,5-trifluorobenzyloxy)-3,5-difluorophenyl)-3-fluorophenyl]-5-propyl-1,3-dioxane [ No CAS ]

References: [1]Patent: CN105358538,2016,A .

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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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Product Details of 4-Bromo-3-fluorobenzaldehyde

Safety of 4-Bromo-3-fluorobenzaldehyde

Application In Synthesis of 4-Bromo-3-fluorobenzaldehyde

[ 133059-43-5 ] Synthesis Path-Downstream 1~7

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