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[ CAS No. 348-27-6 ]

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Chemical Structure| 348-27-6
Chemical Structure| 348-27-6
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CAS No. :348-27-6 MDL No. :MFCD06797918
Formula : C7H5FO2 Boiling Point : 254.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :140.11 g/mol Pubchem ID :587246
Synonyms :

Safety of [ 348-27-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 348-27-6 ]

  • Upstream synthesis route of [ 348-27-6 ]
  • Downstream synthetic route of [ 348-27-6 ]

[ 348-27-6 ] Synthesis Path-Upstream   1~11

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  • [ 348-27-6 ]
  • [ 55660-73-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 7-8, p. 1027 - 1034
  • 2
  • [ 348-27-6 ]
  • [ 54788-19-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 39 - 44
  • 3
  • [ 331-64-6 ]
  • [ 348-27-6 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With aluminum (III) chloride In dichloromethane for 72 h; Reflux
Stage #2: With water In dichloromethaneCooling with ice-water
To a 2000 mL dry round bottom flask were added 2-fluoro-4-methoxybenzaldehyde (25.0 g, 162.2 mmol), anhydrous AlCl3 (64.8 g, 486.8 mmol) and anhydrous CH2Cl2 (1000 mL). The mixture was stirred and refluxed for 3 days. The reaction mixture was cooled in an ice-water bath, then ice (100 g) was added very carefully into the reaction mixture to quench the excess AlCl3. Another 800 mL of cold water was added. The organic layer was separated, and the aqueous solution was extracted with MTBE (300 mL.x.2). The combined organic layer was concentrated, and the residual solid was dissolved in 400 mL of cold 2N aqueous NaOH and 200 mL of water. The resulting aqueous solution was extracted with MTBE (200 mL.x.2). The basic aqueous solution then was acidified with concentrated HCl. After filtration and drying, 2-fluoro-4-hydroxybenzaldehyde (21.5 g) was obtained as a white solid. Yield: 95percent. 1H NMR (Acetone-d6, 300 MHz): δ=10.12 (s, 1H), 9.87 (s, 1H), 7.74 (t, J=8.4 Hz, 1H), 6.83 (dd, J=8.4, 1.8 Hz, 1H), 7.70 (dd, J=12.3, 2.1 Hz, 1H).
86%
Stage #1: With boron tribromide In dichloromethane at -70 - 20℃;
Stage #2: With water In dichloromethane for 0.5 h;
To a -70 0C solution of 2-fluoro-4-methoxy-benzaldehyde (19.1 g, 120 mmol) in CH2CI2 (100 ml.) was added boron tribromide in CH2CI2 (1 M, 160 ml_, 160 mmol). After stirring the reaction solution at -68 0C for 45 min the cooling bath was removed, and the solution was further stirred at room temperature over night. The reaction solution was poured into ice water and stirred for 30 min. The formed precipitate was separated, washed with CH2CI2, and dissolved in EtOAc. The resultant EtOAc phase was washed with water and dried over MgSO4. After evaporation of the solvent the residue was washed with little CH2CI2 and dried in vacuo to give the product as a beige solid. EPO <DP n="32"/>Yield: 14.5 g (86percent) ESI-MS: m/z = 139 [M-H]"
86%
Stage #1: With boron tribromide In dichloromethane at -70 - 20℃;
Stage #2: With water In dichloromethane at 0℃; for 0.5 h;
To a -70 0C solution of 2-fluoro-4-methoxy-benzaldehyde (19.1 g, 120 mmol) in CH2CI2 (100 ml.) was added boron tribromide in CH2CI2 (1 M, 160 ml_, 160 mmol). After stirring the reaction solution at -68 0C for 45 min the cooling bath was removed, and the solution was further stirred at room temperature over night. The reaction solution was poured into ice water and stirred for 30 min. The formed precipitate was separated, washed with CH2CI2, and dissolved in EtOAc. The resultant EtOAc phase was washed with water and dried over MgSO4. After evaporation of the solvent the residue was washed with little CH2CI2 and dried in vacuo to give the product as a beige solid. Yield: 14.5 g (86percent) <n="46"/>ESI-MS: m/z = 139 [M-H]"
80.6%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃;
Stage #2: With water In dichloromethane
Intermediate 24. 5-bromo-2-fluoro-4-hydroxybenzaldehyde (24); [0196] To the solution of 2-fluoro-4-methoxybenzaldehyde (3 g, 19.5 mmol, 1 eq., Aldrich, Milwaukee, WI, USA) in DCM (80 mL) was added dropwise BBr3 (14.5 g, 58.7 mmol, 3 eq.) at 0°C. The mixture was stirred for 15 min, then warmed to room temperature and continued to stir for additional 3 h. The reaction was quenched by careful addition of water (50 mL), the organic layer was separated, and remaining the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic layers were concentrated in vacuo and purified by silica gel chromatography (DCM:MeOH = 25: 1 to 10:1) to afford 2.2 g (80.6percent) of 2-fluoro-4-hydroxybenzaldehyde (24).
80.6%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; for 3.25 h;
Stage #2: With water In dichloromethane
[0155] To the solution of 2-fluoro-4-methoxybenzaldehyde (3 g, 19.5 mmol, 1 eq.) in DCM (80 mL) was added dropwise BBr3 (14.5 g, 58.7 mmol, 3 eq.) at 00C. The mixture was stirred for 15 min, then warmed to rt. and continued to stir for additional 3h. The reaction was quenched by careful addition of water (50 mL), the organic layer was separated, and remaining the aqueous layer was extracted with DCM (2x50 mL). The combined organic layers were concentrated in vacuo and purified by silica gel chromatography (DCM:MeOH = 25: 1 to 10: 1) to afford 2.2 g (80.6 percent) of 2- fluoro-4-hydroxybenzaldehyde (10).

Reference: [1] Patent: US2011/98251, 2011, A1, . Location in patent: Page/Page column 67-68
[2] Chemistry Letters, 2008, vol. 37, # 4, p. 436 - 437
[3] Patent: WO2007/14895, 2007, A2, . Location in patent: Page/Page column 30; 31
[4] Patent: WO2008/87198, 2008, A1, . Location in patent: Page/Page column 44-45
[5] Patent: WO2010/102154, 2010, A2, . Location in patent: Page/Page column 55
[6] Patent: WO2011/2814, 2011, A2, . Location in patent: Page/Page column 47
  • 4
  • [ 372-20-3 ]
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Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 39 - 44
  • 5
  • [ 175968-16-8 ]
  • [ 348-27-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 14, p. 3145 - 3147
  • 6
  • [ 114635-97-1 ]
  • [ 348-27-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 14, p. 3145 - 3147
  • 7
  • [ 68-12-2 ]
  • [ 114635-97-1 ]
  • [ 348-27-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 39 - 44
  • 8
  • [ 348-27-6 ]
  • [ 74-88-4 ]
  • [ 331-64-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 39 - 44
  • 9
  • [ 348-27-6 ]
  • [ 96740-92-0 ]
Reference: [1] Chemistry Letters, 2008, vol. 37, # 4, p. 436 - 437
[2] Journal of Medicinal Chemistry, 2015, vol. 57, # 21, p. 8984 - 8998
  • 10
  • [ 348-27-6 ]
  • [ 75-03-6 ]
  • [ 532965-74-5 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide at 25 - 60℃; for 10 h; Inert atmosphere To a mixture of 2-fluoro-4-hydroxy-benzaldehyde (1.0 g, 7.1 mmol) and potassium carbonate (2.0 g, 14 mmol) in N, N-dimethylformamide ( 10 mL) at 25 °C under nitrogen was added iodoethane (1.1 g, 7.1 mmol). The mixture was stirred at 60 °C for 10 hours, concentrated in vacuo, diluted with ethyl acetate (200 mL), washed with saturated sodium bicarbonate solution (3 x 50 mL) and brine (3 x 50 mL), dried with anhydrous sodium sulfate and concentrated in vacuo to give compound B-238 (1.0 g, 83percent yield) as a red solid. -NMR (CD3OD, 400 MHz): 10.09 (s, 7.76-7.67 (m, IH), 6.83-6.74 (m, 2H), 4.11 (t, J=6.8 Hz, 2H), 1.40 (t, J=7.0 Hz, 3H).
Reference: [1] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00537-00538
[2] Patent: WO2016/201096, 2016, A1, . Location in patent: Paragraph 00335
  • 11
  • [ 348-27-6 ]
  • [ 100-39-0 ]
  • [ 504414-32-8 ]
YieldReaction ConditionsOperation in experiment
94.4% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 72 h; Example 2: 10-acetyl-l l-(4-benzyloxy-2-fluorophenyl)-3,3-dimethyl-l,l-dioxo- 1,2,3,4,5,1 l-hexahvdro-lλ6-thia-5J0-diazadibenzorα,πcvcloheptene (13); Step 1; A mixture of 2-fluoro-4-hydroxybenzaldehyde (2.92 mmol), benzylbromide (534 μL, 4.38 mmol) and Cs2CO3 (1.14 g, 3.50 mmol) in dry DMF (N,N-dimethylformamide; <n="51"/>10 niL) was stirred at room temperature for 3 days. Then, the reaction mixture was diluted with water (200 mL). The resulting precipitate was filtered off, then dried under vacuum to give the desired product 4-benzyloxy-2-fluorobenzaldehyde (11) (94.4 percent) as a white solid: m/z = 231 (M+H)+.
Reference: [1] Patent: WO2008/99020, 2008, A1, . Location in patent: Page/Page column 49-50
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