[ CAS No. 320-76-3 ] {[proInfo.proName]}

Name: 320-76-3|4-Bromo-2-fluoro-6-nitrophenol|98%
Brand: Ambeed
SKU: A128312
Price: 6.0 USD
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Quality Control of [ 320-76-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 320-76-3 ]

Product Details of [ 320-76-3 ]

CAS No. :	320-76-3	MDL No. :	MFCD00013372
Formula :	C₆H₃BrFNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ACQVEWFMUBXEMR-UHFFFAOYSA-N
M.W :	236.00	Pubchem ID :	688116
Synonyms :

Calculated chemistry of [ 320-76-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.95
TPSA :	66.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.53
Log Po/w (XLOGP3) :	2.74
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	0.36
Consensus Log Po/w :	1.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.11 mg/ml ; 0.000464 mol/l
Class :	Soluble
Log S (Ali) :	-3.78
Solubility :	0.039 mg/ml ; 0.000165 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.34
Solubility :	1.07 mg/ml ; 0.00455 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 320-76-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H315-H317-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 320-76-3 ]

* 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.

Upstream synthesis route of [ 320-76-3 ]
Downstream synthetic route of [ 320-76-3 ]

[ 320-76-3 ] Synthesis Path-Upstream 1~7

1
[ 320-76-3 ]
[ 394-50-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

2
[ 320-76-3 ]
[ 437-83-2 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

3
[ 2105-94-4 ]
[ 320-76-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

4
[ 367-12-4 ]
[ 320-76-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

5
[ 403-19-0 ]
[ 320-76-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

6
[ 576-86-3 ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1872

7
[ 399-96-2 ]
[ 320-76-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178

[ 320-76-3 ] Synthesis Path-Downstream 1~32

1
[ 576-86-3 ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1872

2
[ 2105-94-4 ]
[ 320-76-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

3
[ 320-76-3 ]
[ 77-78-1 ]
[ 74266-66-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

4
[ 576-86-3 ]
[ 64-19-7 ]
NaNO₂ [ No CAS ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1872

5
[ 51321-61-0 ]
[ 320-76-3 ]
[ 452912-13-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1713 - 1716

6
[ 320-76-3 ]
[ 452912-20-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1713 - 1716

7
[ 320-76-3 ]
4'-[2-[bis-(isopropyl)-amino]-2-oxoethoxy]-3'-fluoro-5'-nitro-(1,1'-biphenyl)-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1713 - 1716

8
[ 367-12-4 ]
[ 320-76-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

9
[ 403-19-0 ]
[ 320-76-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

10
[ 399-96-2 ]
[ 320-76-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

11
[ 320-76-3 ]
[ 394-50-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

12
[ 320-76-3 ]
[ 437-83-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

13
[ 320-76-3 ]
[ 74266-68-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. 2,p. 175 - 178

14
sodium dithionite [ No CAS ]
[ 320-76-3 ]
[ 140-89-6 ]
[ 182499-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; for 1.5h;Heating / reflux;	Preparation of 5-bromo-7-fluoro-2-(methylthio)-benzoxazole (P1) A solution of 8.55 g of sodium dithionite in 40 ml of water is added to 2 g of <strong>[320-76-3]4-bromo-2-fluoro-6-nitro-phenol</strong> in 100 ml of ethanol, and the reaction medium is heated under reflux for 1 hour 30 minutes. After cooling down, the solution is filtered, evaporation is carried out until a dry extract is obtained which is taken up in ethyl acetate and washed, then the organic phase is dried. The residue (2-amino-4-bromo-6-fluoro-phenol) is re-evaporated under reduced pressure with 80 ml of methanol, 12.5 ml of water, 1.86 g of potassium ethyl xanthogenate and the reaction medium is heated under reflux for 4 hours (5-bromo-7-fluoro-2-(3H)-benzoxazolethione is obtained).

Reference： [1]Patent: US2004/225111,2004,A1 .Location in patent: Page 21-22

15
[ 320-76-3 ]
[ 106-95-6 ]
[ 865716-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 45℃;	Example 89A 2-(allyloxy)-5-bromo-1-fluoro-3-nitrobenzene A mixture of 4-bromo-6-fluoro-2-nitrophenol (2 g, 8.49 mmol), allyl bromide (0.88 mL, 10.07 mmol) and K2CO3 (2.34 g, 16.98 mmol) in DMF (20 mL) was stirred at 45 C. overnight. Inorganic salts were filtered off, and the filtrate was concentrated to provide the crude product, which was directly used for next step without further purification. MS (DCI/NH3) m/z 245.92 (M+H)+; 1H NMR (400 MHz, DMSO-D6) delta ppm 4.70 (d, J=6.14 Hz, 2H) 5.27 (d, J=10.43 Hz, 1H) 5.37 (dd, J=17.18, 1.53 Hz, 1H) 5.92-6.02 (m, 1H) 8.03-8.06 (m, 2H).

Reference： [1]Patent: US2005/215556,2005,A1 .Location in patent: Page/Page column 82

16
[ 320-76-3 ]
[ 7772-99-8 ]
[ 182499-89-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol;	a) Preparation of 2-amino-6-fluoro-4-bromophenol A mixture of <strong>[320-76-3]4-bromo-2-fluoro 6-nitrophenol</strong>(1 g, 4.2 mmol) and tin (II) chloride (4.78 g, 21.2 mmol) in ethanol(50 mL) was heated at 80 C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(710 mg, 82%). 1 H NMR (CD3 OD): delta 6.51-6.40 (m, 2H).
82%	In ethanol;	a)Preparation of 2-amino-6-fluoro-4-bromophenol A mixture of <strong>[320-76-3]4-bromo-2-fluoro 6-nitrophenol</strong>(1 g, 4.2 mmol) and tin (II) chloride (4.78 g, 21.2 mmol) in ethanol(50 mL) was heated at 80 C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(710 mg, 82%). 1 H NMR (CD3 OD): d 6.51-6.40 (m, 2H).
82%	In ethanol;	a) Preparation of 2-amino-6-fluoro-4-bromophenol A mixture of <strong>[320-76-3]4-bromo-2-fluoro 6-nitrophenol</strong> (1 g, 4.2 mmol) and tin (II) chloride (4.78 g, 21.2 mmol) in ethanol (50 mL) was heated at 80 C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product (710 mg, 82%). 1H NMR (CD3OD): d 6.51-6.40 (m, 2H).

Reference： [1]Patent: US5886044,1999,A
[2]Patent: US5780483,1998,A
[3]Patent: US6262113,2001,B1

17
[ 320-76-3 ]
[ 105-36-2 ]
ethyl 2-(4-bromo-2-fluoro-6-nitrophenoxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 1.0h;	To a suspension of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (20.0 g, 84.7 mmol) and K2CO3 (12.9 g, 93.2 mmol) in DMSO (150 ml) was added ethyl bromoacetate (10.4 ml, 93.2 mmol) at room temperature. After stirring 1 hr at 800C, the reaction mixture was treated with EtOAc and H2O. The organic layer was separated, washed successively with H2O and brine, dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in AcOH (150 ml). Fe (14.2 g, 254 mmol) was added to the resultant solution at room temperature. After stirring for 3 hr at 900C, the reaction mixture was filtrated, and the filtrate was concentrated in vacuo. The residue was treated with THF, EtOAc and brine. The organic layer was separated, washed with brine and concentrated in vacuo. The residue was recrystallized from THF, EtOAc and hexane to give the title compound (13.24 g, 64%) .1H-NMR (300 MHz, DMSO-d6) delta: 4.68 (2 H, s), 6.87 (1 H, t, J = 2.0 Hz), 7.21 (1 H, dd, J=IO.0, 2.0 Hz), 10.99 (1 H, s) .
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 12.0h;Inert atmosphere;	Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed a <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (500 mg, 2.119 mmol, 1.00 equiv.) in DMF (10 mL), ethyl 2-bromoacetate (424 mg, 2.539 mmol, 1.20 equiv.) and K2CO3 (588 mg, 4.255 mmol, 2.00 equiv.). The resulting solution was stirred 12 h at 60 C. The reaction was monitored by TLC. The resulting solution was extracted with EtOAc, then the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with EA/PE (1:10) to yield ethyl 2-(4-bromo-2-fluoro-6-nitrophenoxy)acetate as a yellow solid. 1H NMR (400 MHz, CDCl3) delta: 7.79-7.77 (m, 1H), 7.52-7.49 (m, 1H), 4.80 (s, 2H), 4.27-4.22 (m, 2H), 1.32-1.26 (m, 3H
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 12.0h;Inert atmosphere;	Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed a <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (500 mg, 2.119 mmol, 1.00 equiv.) in DMF (10 mL), ethyl 2-bromoacetate (424 mg, 2.539 mmol, 1.20 equiv.) and K2CO3 (588 mg, 4.255 mmol, 2.00 equiv.). The resulting solution was stirred 12 h at 60 C. The reaction was monitored by TLC. The resulting solution was extracted with EtOAc, then the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with EA/PE (1:10) to yield ethyl 2-(4-bromo-2-fluoro-6-nitrophenoxy)acetate as a yellow solid. 1H NMR (400 MHz, CDCl3) delta: 7.79-7.77 (m, 1H), 7.52-7.49 (m, 1H), 4.80 (s, 2H), 4.27-4.22 (m, 2H), 1.32-1.26 (m, 3H

With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 12.0h;Inert atmosphere;

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed a <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (500 mg, 2.119 mmol, 1.00 equiv.) in DMF (10 mL), ethyl 2-bromoacetate (424 mg, 2.539 mmol, 1.20 equiv.) and K2CO3 (588 mg, 4.255 mmol, 2.00 equiv.). The resulting solution was stirred 12 h at 60 C. The reaction was monitored by TLC. The resulting solution was extracted with EtOAc, then the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with EA/PE (1:10) to yield ethyl 2-(4-bromo-2-fluoro-6-nitrophenoxy)acetate as a yellow solid. 1H NMR (400 MHz, CDCl3) delta: 7.79-7.77 (m, 1H), 7.52-7.49 (m, 1H), 4.80 (s, 2H), 4.27-4.22 (m, 2H), 1.32-1.26 (m, 3H

Reference： [1]Patent: WO2007/77961,2007,A2 .Location in patent: Page/Page column 305
[2]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 1227; 1228; 1229; 1230
[3]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 1197-1198
[4]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 1214-1216

18
[ 320-76-3 ]
[ 96-32-2 ]
[ 943994-29-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 65℃;	A mixture of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (216 g, 917 mmol), methyl 2-bromoacetate (104 ml, 1.10 mol) and K2CO3 (633 g, 4.58 mol) in DMF (500 ml) was heated at 65C overnight. The reaction mixture was poured into water and the off-white precipitate was collected by filtration and to give the title compound (282 g, 99%) . This compound was taken onto the next step as is. LCMS (ESI"), M-H+: 307.
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Compound 14 was synthesised from <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> using same procedure as mentioned for 9d using DMF as solvent in 85% yield. 1H NMR (300 MHz, CDCl3) delta = 3.80 (s, 3H), 4.83 (s, 2H), 7.53 (d, J = 10.17 Hz, 1H), 7.80 (s,1H); 13C NMR (300 MHz, CDCl3) delta= 52.50, 70.0, 115.54, 123.69, 139.34, 145.00, 153.63, 157.01, 168.03; HRMS m/z (EI) calcd. for C9H7BrFNO5 306.9492, found 307.9573 [M+H]+

Reference： [1]Patent: WO2007/77961,2007,A2 .Location in patent: Page/Page column 296
[2]Synthetic Communications,2013,vol. 43,p. 3315 - 3321
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631

19
[ 320-76-3 ]
[ 560082-53-3 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631
[2]Synthetic Communications,2013,vol. 43,p. 3315 - 3321
[3]Patent: US2019/47960,2019,A1
[4]Patent: US2019/47961,2019,A1
[5]Patent: WO2019/86890,2019,A1

20
[ 320-76-3 ]
6-acetyl-8-fluoro-2H-1,4-benzoxazin-3(4H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631

21
[ 320-76-3 ]
4,4,4-trifluoro-1-(8-fluoro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)-butane-1,3-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631

22
[ 320-76-3 ]
8-fluoro-6-[1-(4-fluoro-2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-2H-1,4-benzoxazin-3(4H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631

23
[ 320-76-3 ]
[ 711022-49-0 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 3315 - 3321

24
[ 320-76-3 ]
[ 182499-89-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With aluminum (III) chloride; ethanol; iron; In water; for 3.0h;Reflux;	To a solution of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (8.0g, 33.9mmol) in EtOH:H20 (4: 1 , 100ml_) were added Fe powder (9.1 g, 169.4mmol) and AICI3 (22.5g, 169.4mmol) at rt. The reaction mixture was stirred and refluxed for 3h. The TLC showed reaction to be complete. The reaction mixture was filtered through a celite bed. The celite bed was further washed with EtOH (50ml_). The solvent was evaporated under reduced pressure. The residue was diluted with H20 (50ml_) and extracted with EtOAc (3X50ml_). The combined organic layer was dried (Na2S04), filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 0-5% EtOAc in hexane to afford 2-amino-4-bromo-6-fluorophenol as a brown solid. Yield: 6.2g (90%). MS (ESI-) for CHNOS m/z 203.89 [M-H]+.
76.4%	With tin(II) chloride dihdyrate; In ethanol; for 2.0h;Reflux;	At room temperature, 204 SnCl2.2H2O (14.3 g, 63.50 mmol) was added into 205 <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (3.00 g, 12.7 mmol) in 105 ethanol (100 mL), and the reaction was refluxed for 2 hrs. After cooling to room temperature, it was added into ice-water, and the stirring was continued for 0.5 hrs. Ethanol was removed under reduce pressure, extracted with ethyl acetate (100 mL×3), the combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2.0 g of a pale yellow solid, yield was 76.4%, LC-MS(APCI): m/z=206.1 (M+1).
70%	With tin(ll) chloride; In ethanol; at 80℃; for 2.0h;	To a stirred solution of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (15 g, 0.072 mol) in EtOH (0616) (750 mL) was added SnCl2 (67.5 g, 0.36 mol). The reaction mixture was heated at 80C for 2 h, then poured into ice. The pH was adjusted to 7-8 using aqueous NaOH solution, then the aqueous layer was extracted with EtOAc (2 x 600 mL). The combined organic layer was dried over anhydrous Na2S04, then concentrated, to afford the title compound (10.5 g, 70%) as a grey solid. deltaEta (400 MHz, DMSO-de) 9.21 (s, 1H), 6.72-6.45 (m, 2H), 5.17 (br s, 2H)

Reference： [1]Patent: WO2019/86890,2019,A1 .Location in patent: Page/Page column 93
[2]Patent: US2019/152954,2019,A1 .Location in patent: Paragraph 0373; 0374
[3]Patent: WO2016/198400,2016,A1 .Location in patent: Page/Page column 61

25
[ 320-76-3 ]
[ 509147-84-6 ]

Reference： [1]Patent: WO2016/198400,2016,A1

26
[ 320-76-3 ]
2-chloro-1-fluoro-5-methyl-3-nitrobenzene [ No CAS ]

Reference： [1]Patent: WO2017/85198,2017,A1

27
[ 320-76-3 ]
5-bromo-2-chloro-1-fluoro-3-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With oxalyl dichloride; In N,N-dimethyl-formamide; at -30 - 80℃; for 4.75h;Inert atmosphere;	To a solution of 4-Bromo-2-fluoro-6-nitrophenol (500 mg, 2.06 mmol) in anhydrous DMF (5 mL) at -30/40C is added oxalyl chloride (0.35 mL, 4.11 mmol, 2 eq), dropwise. The resulting white heterogeneous mixture is then stirred for 15 min at -40C and heated up to 80C for 4h30. The RM is cooled to RT. Ice and water (20 mL) are successively added and the mixture is stirred further for 20 min. The yellow precipitate is collected by filtration and dried under HV to afford the title compound as a yellow solid (418 mg, 79%). LC- MS A: tR = 0.89 min; no ionization.

Reference： [1]Patent: WO2017/85198,2017,A1 .Location in patent: Page/Page column 135

28
[ 320-76-3 ]
6-bromo-8-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]

Reference： [1]Patent: US2019/47960,2019,A1
[2]Patent: US2019/47961,2019,A1

29
[ 320-76-3 ]
6-bromo-4-ethyl-8-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]

Reference： [1]Patent: US2019/47961,2019,A1
[2]Patent: US2019/47960,2019,A1

30
[ 320-76-3 ]
[ 106-93-4 ]
5-bromo-2-(2-bromoethoxy)-1-fluoro-3-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3.0h;	Into a 250-mL round bottle, to a solution of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (5.00 g, 21 mmol, 1.00 equiv.) in DMF (50 mL). 1,2-Dibromoethane (5.90 g, 31 mmol, 1.50 equiv.), K2CO3 (5.80 g, 42 mmol, 2.00 equiv.) were added and the mixture was stirred for 3 h at 80 C. The mixture was quenched by the addition of H2O, extracted with EA, the organic layers was concentrated under vacuum. The residue purified by silica gel with ethyl acetate/petroleum ether (5:95). The collected fractions were combined and concentrated under vacuum to yield 5-bromo-2-(2-bromoethoxy)-1-fluoro-3-nitrobenzene as yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.79 (t, J=2.2 Hz, 1H), 7.56 (d, J=9.9 Hz, 1H), 4.52 (t, J=6.4, Hz, 2H), 3.64-3.88 (m, 2H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3.0h;	Into a 250-mL round bottle, to a solution of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (5.00 g, 21 mmol, 1.00 equiv.) in DMF (50 mL). 1,2-Dibromoethane (5.90 g, 31 mmol, 1.50 equiv.), K2CO3 (5.80 g, 42 mmol, 2.00 equiv.) were added anf the mixture was stirred for 3 h at 80 C. The mixture was quenched by the addition of H2O, extracted with EA, the organic layers was concentrated under vacuum. The residue purified by silica gel with ethyl acetate/petroleum ether (5:95). The collected fractions were combined and concentrated under vacuum to yield 5-bromo-2-(2-bromoethoxy)-1-fluoro-3-nitrobenzene as yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.79 (t, J=2.2 Hz, 1H), 7.56 (d, J=9.9 Hz, 1H), 4.52 (t, J=6.4, Hz, 2H), 3.64-3.88 (m, 2H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3.0h;	Into a 250-mL round bottle, to a solution of <strong>[320-76-3]4-bromo-2-fluoro-6-nitrophenol</strong> (5.00 g, 21 mmol, 1.00 equiv.) in DMF (50 mL). 1,2-Dibromoethane (5.90 g, 31 mmol, 1.50 equiv.), K2CO3 (5.80 g, 42 mmol, 2.00 equiv.) were added anf the mixture was stirred for 3 h at 80 C. The mixture was quenched by the addition of H2O, extracted with EA, the organic layers was concentrated under vacuum. The residue purified by silica gel with ethyl acetate/petroleum ether (5:95). The collected fractions were combined and concentrated under vacuum to yield 5-bromo-2-(2-bromoethoxy)-1-fluoro-3-nitrobenzene as yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.79 (t, J=2.2 Hz, 1H), 7.56 (d, J=9.9 Hz, 1H), 4.52 (t, J=6.4, Hz, 2H), 3.64-3.88 (m, 2H).

Reference： [1]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 1218; 1219; 1220
[2]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 1188-1189
[3]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 1205-1207

31
[ 320-76-3 ]
6-bromo-4-ethyl-8-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]

Reference： [1]Patent: US2019/47961,2019,A1
[2]Patent: US2019/47960,2019,A1

32
[ 320-76-3 ]
5-bromo-7-fluoro-2-methylbenzo[d]oxazole [ No CAS ]

Reference： [1]Patent: US2019/152954,2019,A1

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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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.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
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H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
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

[ CAS No. 320-76-3 ] {[proInfo.proName]}

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[ 320-76-3 ] Synthesis Path-Upstream 1~7

[ 320-76-3 ] Synthesis Path-Downstream 1~32

Related Functional Groups of [ 320-76-3 ]

Fluorinated Building Blocks

Aryls

Bromides

Nitroes

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[ 320-76-3 ]