[ CAS No. 914637-27-7 ]

Name: 914637-27-7|(3-Fluoro-5-methoxyphenyl)methanol|98%
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Quality Control of [ 914637-27-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 914637-27-7 ]

CAS No. :	914637-27-7	MDL No. :	MFCD08741377
Formula :	C₈H₉FO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AKNFFYDXPZERQS-UHFFFAOYSA-N
M.W :	156.15 g/mol	Pubchem ID :	26985456
Synonyms :

Safety of [ 914637-27-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2810
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 914637-27-7 ]

* 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.

Upstream synthesis route of [ 914637-27-7 ]
Downstream synthetic route of [ 914637-27-7 ]

[ 914637-27-7 ] Synthesis Path-Upstream 1~1

1
[ 914637-27-7 ]
[ 914637-31-3 ]

Reference： [1] Patent: WO2011/156518, 2011, A2,
[2] Patent: US2016/24059, 2016, A1,

[ 914637-27-7 ] Synthesis Path-Downstream 1~26

2
[ 914637-27-7 ]
[ 1214346-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane at 0℃; for 1h;	20.iii (iii) (3-fluoro-5-methoxyphenyl)acetonitriIeThionyl chloride (0.95 ml) was added to a solution of the product of step (ii) (0.95 ml) in DCM (20 ml) at 0 0C, then stirred for 1 h. The reaction mixture was washed with 2M HCl, EPO the organics were separated then dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in DMF (10 ml) and sodium cyanide (0.3 g) was added. The mixture was stirred for 2 h, then partitioned between ether and water; the organics were separated, then dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 1 : 1 ether/ isohexane) to give the subtitle compound (0.47 g). 1H NMR CDCl3-d6: δ 6.66 (3H, m), 3.81 (3H, s), 3.70 (2H, s).
	With thionyl chloride In DCM at 0℃; for 1h;	66.iii (iii) (3-fluoro-5-methoxyphenyl)acetonitrile Thionyl chloride (0.95 ml) was added to a solution of the product of step (ii) (0.95 ml) in DCM (20 ml) at 0° C., then stirred for 1 h. The reaction mixture was washed with 2M HCl, the organics were separated then dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in DMF (10 ml) and sodium cyanide (0.3 g) was added. The mixture was stirred for 2 h, then partitioned between ether and water; the organics were separated, then dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 1:1 ether/isohexane) to give the subtitle compound (0.47 g). 1H NMR CDCl3-d6: δ 6.66 (3H, m), 3.81 (3H, s), 3.70 (2H, s).
	With phosphorus pentachloride In tetrachloromethane at 20℃; for 1h;	30.3 To a solution of (3-fluoro-5-methoxyphenyl)methanol (4.9 g, 30 mmol) in CC14 (50 mL), PCI5 (13 g, 60 mmol) was added. The mixture was stirred at room temperature for 1 h. To this mixture, saturated Na2C03 solution was slowly added until pH was adjusted to 7~8. The mixture was extracted with DCM (3 x 15 mL), and the organic phase was concentrated to give a colorless oil, which was purified by silica-gel column chromatography (100% petroleum ether) to give 2.9 g of l-(chloromethyl)-3-fluoro-5-methoxybenzene. 1H NMR (CDC13): δ 6.68-6.72 (m, 2H), 6.54-6.59 (m, 1H), 4.51 (s, 2H), 3.81 (s, 3H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2007/39736, 2007, A1 Location in patent: Page/Page column 42-43
[2]Current Patent Assignee: ASTRAZENECA PLC - US2008/293775, 2008, A1 Location in patent: Page/Page column 44
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/156518, 2011, A2 Location in patent: Page/Page column 117

3
[ 82477-68-7 ]
[ 914637-27-7 ]

Yield	Reaction Conditions	Operation in experiment
		66.ii (ii) (3-fluoro-5-methoxyphenyl)methanol The subtitle compound was prepared by the method of example 11 step (ii) using the product of step (i). 1H NMR CDCl3-d6: δ 6.68 (2H, m), 6.53 (1H, m), 4.67 (2H, d), 3.8 (3H, s).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2008/293775, 2008, A1 Location in patent: Page/Page column 44

4
[ 455-40-3 ]
[ 914637-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 12 h / 120 °C 1.2: pH 3 - 4 2.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/156518, 2011, A2

5
[ 176548-72-4 ]
[ 914637-27-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[176548-72-4]3-fluoro-5-methoxybenzoic acid</strong> (5.1 g, 30 mmol) in dry ether at 0 C, L1AIH4 (3.44 g, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 h, and quenched by slow addition of 1 M aqueous HC1 solution (30 mL). The mixture was extracted with ethyl acetate (3 x 15 mL). The organic phase was dried over Na2S04 and concentrated to give 4.9 g of (3-fluoro-5-methoxyphenyl)methanol. ¾ NMR (CDCI3): delta 6.67-6.70 (m, 2H), 6.50-6.55 (m, 1H), 4.64 (d, 2H), 3.79 (s, 3H).

Reference： [1]Patent: WO2011/156518,2011,A2 .Location in patent: Page/Page column 117

6
[ 914637-27-7 ]
[ 914637-31-3 ]

Reference： [1]Patent: WO2011/156518,2011,A2
[2]Patent: US2016/24059,2016,A1

7
[ 914637-27-7 ]
[ 914637-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: phosphorus pentachloride / tetrachloromethane / 1 h / 20 °C 2.1: potassium iodide / water; dimethyl sulfoxide / 6 h / 45 °C 3.1: sodium hydroxide; water / methanol / 4 h / 65 °C 3.2: 20 °C / pH 4 - 5

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/156518, 2011, A2

8
[ 914637-27-7 ]
[ 1352306-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: phosphorus pentachloride / tetrachloromethane / 1 h / 20 °C 2.1: potassium iodide / water; dimethyl sulfoxide / 6 h / 45 °C 3.1: sodium hydroxide; water / methanol / 4 h / 65 °C 3.2: 20 °C / pH 4 - 5 4.1: polyphosphoric acid / 3 h / 80 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/156518, 2011, A2

9
[ 29578-39-0 ]
[ 914637-27-7 ]

Reference： [1]Patent: US2016/24059,2016,A1

10
C₉H₉FO₃ [ No CAS ]
[ 914637-27-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With lithium aluminium tetrahydride In tetrahydrofuran at -50 - 0℃; for 3h;	23 Example 23 Preparation of intermediate 6-Bromomethyl-8-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (D-9) To a solution of D-9-1 (250 g, 1.4 mol) in THF (2000 mL), cooled to -50 C, is added LAH (77 g, 2.0 mol). The mixture is slowly warmed to 0° C. and stirred for 3 h. Excess reactants are consumed by the addition of a aqueous solution of NH4Cl and the mixture is extracted with EtOAc. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by flash silica gel chromatography to afford D-9-2 (100 g, 47% yield).

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2016/24059, 2016, A1 Location in patent: Paragraph 0376; 0378

11
[ 914637-27-7 ]
6-bromomethyl-8-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: hydrogen bromide / water; toluene / 24 h / 20 °C 2.1: acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: ammonium hydroxide; hydrogen; nickel / methanol / 5 h / 20 °C / 1551.49 Torr 4.1: formic acid / 50 °C 5.1: hydrogen bromide / water / 48 h / 90 °C 6.1: triethylamine / water; tetrahydrofuran / 3 h / 20 °C 7.1: triethylamine / dichloromethane / 3 h / 20 °C 8.1: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine / 48 h / 90 °C / 22502.3 Torr 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -50 - 0 °C 10.1: dibromotriphenylphosphorane; pyridine / dichloromethane / 3 h / 0 °C