Home Cart 0 Sign in  

[ CAS No. 1114809-02-7 ]

{[proInfo.proName]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1114809-02-7
Chemical Structure| 1114809-02-7
Structure of 1114809-02-7 *Storage: {[proInfo.prStorage]}

Quality Control of [ 1114809-02-7 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 1114809-02-7 ]

SDS

Product Details of [ 1114809-02-7 ]

CAS No. :1114809-02-7MDL No. :MFCD11520661
Formula :C7H3BrClFOBoiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :237.45Pubchem ID :56971740
Synonyms :

Computed Properties of [ 1114809-02-7 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1114809-02-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P301 P312-P302 P352-P304 P340-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1114809-02-7 ]

  • Downstream synthetic route of [ 1114809-02-7 ]

[ 1114809-02-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1114809-02-7 ]
  • 7-chloro-4-phenylbenzo[b]thiophene [ No CAS ]
  • 2
  • [ 1114809-02-7 ]
  • C8H4BrClS [ No CAS ]
  • 3
  • [ 34301-54-7 ]
  • [ 1114809-02-7 ]
  • 2-(1-Adamantylsulfanyl)-4-bromo-1-chloro-3-(ethynyl)benzene [ No CAS ]
  • 4
  • [ 34301-54-7 ]
  • [ 1114809-02-7 ]
  • 2-(1-Adamantylsulfanyl)-6-bromo-3-chlorobenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a suspension of NaH (592 mg, ca. 60%in mineral oil, washed with hexane, ca. 15 mmol) in N,N-dimethylformamide (DMF, 13 mL) was added1-adamantanethiol (2.17 g, 12.9 mmol) in DMF (20 mL) at 0 C under N2. The reaction mixture wasstirred at 0 C for 1.5 h, and a solution of 1a (2.97 g, 10.5 mmol) in DMF (20 mL) was added at -40 C.The reaction mixture was stirred at -40 C for 2 h. The reaction mixture was poured into water, andextracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. The filtratewas concentrated under reduced pressure, and purified by silica gel column chromatography(hexane-EtOAc, 4:1) to give 4.27 g (9.93 mmol) of 2a.
  • 5
  • [ 1114809-02-7 ]
  • 3-chloro-2-(difluoromethoxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde [ No CAS ]
  • 6
  • [ 1114809-02-7 ]
  • 6-bromo-3-chloro-2-(difluoromethoxy)benzaldehyde [ No CAS ]
  • 7
  • [ 1114809-02-7 ]
  • 6-bromo-3-chloro-2-hydroxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.1% With potassium hydroxide; In water; dimethyl sulfoxide; at 60℃; for 16h; To a solution of 4-bromo-l-chloro-2-fluorobenzene (23 g, 109.81 mmol, 1 eq) in THF (200 mL) was added LDA (2 M, 65.89 mL, 1.2 eq) at -70C. The mixture was stirred at -70C for 2 h, and to it was added DMF (12.04 g, 164.72 mmol, 12.67 mL, 1.5 eq). The mixture was stirred at -70C for 1 h. Water (100 mL) and aqueous NH4Cl (100 mL) were added to the reaction mixture at 0C. The aqueous phase was extracted with ethyl acetate (100 mL x 3). The combined organic phase was washed with brine (150 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by Combi Flash (1000 mesh silica gel, petroleum ether/ethyl acetate = 80/1 to 50/1) to afford 6-bromo-3-chloro-2-fluoro benzaldehyde (21 g, 88.44 mmol, 80.53% yield) as a yellow solid. 1H NMR (CDCI3, 400 MHz): d 10.32 (s, 1H), 7.51-7.44 (m, 2H) ppm. To a solution of [1114809-02-7]6-bromo-3-chloro-2-fluorobenzaldehyde (19 g, 80.02 mmol, 1 eq) in DMSO (200 mL) was added a solution of KOH (4.49 g, 80.02 mmol, 1 eq) in H20 (5 mL) at 25C. The mixture was stirred at 60C for 15 h. Then more KOH (4.49 g, 80.02 mmol, 1 eq) in water (5 mL) was added to the mixture at 25C. The mixture was stirred at 60C for one more hour. The residue was poured into ice-water (w/w = 1/1, 150 mL) and was adjusted to pH 5 by 2N HC1 acid. The aqueous phase was extracted with ethyl acetate (150 mL x 3). The combined organic phase was washed with water (100 mL) and brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by combi flash (1000 mesh silica gel, petroleum ether/ethyl acetate = 5/1 to 2/1) to afford 6-bromo-3-chloro-2- hydroxybenzaldehyde (10 g, 42.47 mmol, 53.1% yield) as a yellow solid. 'H NMR (CDCL, 400 MHz): d 12.53 (s, 1H), 10.31 (s, 1H), 7.45 (d, / = 8.4 Hz, 1H), 7.16 (d, / = 8.4 Hz, 1H) ppm. To a mixture of 6-bromo-3-chloro-2-hydroxybenzaldehyde (9 g, 38.22 mmol, 1 eq) and l-[[bromo(difluoro)methyl]-ethoxy-phosphoryl]oxyethane (15.31 g, 57.33 mmol, 1.5 eq) in H20 (100 mL) and MeCN (100 mL) was added a solution of KOH (21.45 g, 382.23 mmol, 10 eq) in H20 (20 mL) at 0C. The mixture was stirred at 0C for 2 h. The residue was poured into ice-water (100 mL). The aqueous phase was extracted with ethyl acetate (100 mL x 3). The combined organic phase was washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by combi flash (1000 mesh silica gel, petroleum ether/ethyl acetate = 3/1, 1/1) to afford 6-bromo-3-chloro-2- (difluoromethoxy)benzaldehyde (4.7 g, 16.46 mmol, 43.1% yield) as a yellow solid. 1H NMR (CDCL, 400 MHz): d 10.28 (s, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.53 (d, J = 8.8 Hz, 1H), 6.69 (t, J = 74.0 Hz, 1H) ppm. To a mixture of 6-bromo-3-chloro-2-(difluoromethoxy)benzaldehyde (1 g, 3.50 mmol, 1 eq) and Pin2B2 (4.45 g, 17.51 mmol, 5 eq) in l,4-dioxane (20 mL) was added KOAc (515.68 mg, 5.25 mmol, 1.5 eq) and Pd(dppf)Cl2 (128.16 mg, 175.15 umol, 0.05 eq) in one portion at 25C. The mixture was stirred at l20C for 2 h under N2. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by Combi Flash (1000 mesh silica gel, petroleum ether/ethyl acetate = 10/1, 3/1) to afford 3-chloro-2- (difluoro methoxy)-6-(4,4,5,5-tetramethyl -l,3,2-dioxaborolan-2-yl)benzaldehyde (0.5 g, 1.50 mmol, 42.9% yield) as yellow oil. 1H NMR (CDCL, 400 MHz): d 10.35 (s, 1H), 7.67 (d, 7 = 8.0 Hz, 1H), 7.41 (d, 7 = 8.0 Hz, 1H), 6.64 (t, 7 = 74.0 Hz, 1H), 1.43 (s, 12H) ppm. To a mixture of 3-chloro-2-(difluoromethoxy)-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl) benzaldehyde (0.33 g, 992.38 umol, 1 eq) in THF (10 mL) was added NaBH4 (168.95 mg, 4.47 mmol, 4.5 eq) at 0C. The mixture was stirred at 0C for 0.5 h. The residue was poured into ice-water (w/w = 1/1, 10 mL) and adjusted to pH = 5. The aqueous phase was extracted with ethyl acetate (10 mL x 3). The combined organic phase was washed with brine (10 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by prep-HPLC (column: Nano-micro Kromasil C18 l00*30mm 5um; mobile phase: [water (0.l%TFA)-ACN]; B%: 35%-45%, 10 min) to afford 5-chloro-4-(difluoromethoxy)benzo[c] [l,2]oxaborol-l(3H)-ol (0.143 g, 605.70 umol, 61.0% yield, 99.28% purity) as a white solid. 1H NMR (DMSO-/ , 400 MHz): 5 9.52 (s, 1H), 7.68 (d, 7 = 8.0 Hz, 1H), 7.61 (d, 7 = 8.0 Hz, 1H), 7.16 (t, 7 = 73.2 Hz, 1H), 5.07 (s, 2H) ppm. MS (ESI): m/z = 233.0 [M-H] HPLC: 99.28% (220 nm), 100% (254 nm).
  • 8
  • [ 1114809-02-7 ]
  • 5-chloro-4-(difluoromethoxy)benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]
  • 9
  • [ 1114809-02-7 ]
  • C14H5Cl2F5O3 [ No CAS ]
  • 10
  • [ 1114809-02-7 ]
  • C15H4(2)H3Cl2F5O4 [ No CAS ]
Historical Records

Related Functional Groups of
[ 1114809-02-7 ]

Fluorinated Building Blocks

Chemical Structure| 1160573-22-7

[ 1160573-22-7 ]

6-Bromo-3-chloro-2,4-difluorobenzaldehyde

Similarity: 0.98

Chemical Structure| 1135531-73-5

[ 1135531-73-5 ]

2-Bromo-4-chloro-6-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1806838-88-9

[ 1806838-88-9 ]

2-Bromo-5-chloro-4-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1056264-66-4

[ 1056264-66-4 ]

2-Bromo-3-chloro-6-fluorobenzaldehyde

Similarity: 0.90

Chemical Structure| 1696224-75-5

[ 1696224-75-5 ]

4-Bromo-3-chloro-2-fluorobenzaldehyde

Similarity: 0.86

Chlorides

Chemical Structure| 1160573-22-7

[ 1160573-22-7 ]

6-Bromo-3-chloro-2,4-difluorobenzaldehyde

Similarity: 0.98

Chemical Structure| 1135531-73-5

[ 1135531-73-5 ]

2-Bromo-4-chloro-6-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1806838-88-9

[ 1806838-88-9 ]

2-Bromo-5-chloro-4-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1056264-66-4

[ 1056264-66-4 ]

2-Bromo-3-chloro-6-fluorobenzaldehyde

Similarity: 0.90

Chemical Structure| 1696224-75-5

[ 1696224-75-5 ]

4-Bromo-3-chloro-2-fluorobenzaldehyde

Similarity: 0.86

Bromides

Chemical Structure| 1160573-22-7

[ 1160573-22-7 ]

6-Bromo-3-chloro-2,4-difluorobenzaldehyde

Similarity: 0.98

Chemical Structure| 1135531-73-5

[ 1135531-73-5 ]

2-Bromo-4-chloro-6-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1806838-88-9

[ 1806838-88-9 ]

2-Bromo-5-chloro-4-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1056264-66-4

[ 1056264-66-4 ]

2-Bromo-3-chloro-6-fluorobenzaldehyde

Similarity: 0.90

Chemical Structure| 1696224-75-5

[ 1696224-75-5 ]

4-Bromo-3-chloro-2-fluorobenzaldehyde

Similarity: 0.86

Aryls

Chemical Structure| 1160573-22-7

[ 1160573-22-7 ]

6-Bromo-3-chloro-2,4-difluorobenzaldehyde

Similarity: 0.98

Chemical Structure| 1135531-73-5

[ 1135531-73-5 ]

2-Bromo-4-chloro-6-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1806838-88-9

[ 1806838-88-9 ]

2-Bromo-5-chloro-4-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1056264-66-4

[ 1056264-66-4 ]

2-Bromo-3-chloro-6-fluorobenzaldehyde

Similarity: 0.90

Chemical Structure| 1696224-75-5

[ 1696224-75-5 ]

4-Bromo-3-chloro-2-fluorobenzaldehyde

Similarity: 0.86

Aldehydes

Chemical Structure| 1160573-22-7

[ 1160573-22-7 ]

6-Bromo-3-chloro-2,4-difluorobenzaldehyde

Similarity: 0.98

Chemical Structure| 1135531-73-5

[ 1135531-73-5 ]

2-Bromo-4-chloro-6-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1806838-88-9

[ 1806838-88-9 ]

2-Bromo-5-chloro-4-fluorobenzaldehyde

Similarity: 0.92

Chemical Structure| 1056264-66-4

[ 1056264-66-4 ]

2-Bromo-3-chloro-6-fluorobenzaldehyde

Similarity: 0.90

Chemical Structure| 1696224-75-5

[ 1696224-75-5 ]

4-Bromo-3-chloro-2-fluorobenzaldehyde

Similarity: 0.86