[ CAS No. 174702-59-1 ]

Name: 174702-59-1|4-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one|95%
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Quality Control of [ 174702-59-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 174702-59-1 ]

CAS No. :	174702-59-1	MDL No. :	MFCD09881709
Formula :	C₁₀H₉BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AHMJTIYXKJRVFF-UHFFFAOYSA-N
M.W :	225.08	Pubchem ID :	10537152
Synonyms :

Calculated chemistry of [ 174702-59-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.0
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	2.93
Log Po/w (WLOGP) :	2.82
Log Po/w (MLOGP) :	2.71
Log Po/w (SILICOS-IT) :	3.47
Consensus Log Po/w :	2.84

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0796 mg/ml ; 0.000354 mol/l
Class :	Soluble
Log S (Ali) :	-2.95
Solubility :	0.252 mg/ml ; 0.00112 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.13
Solubility :	0.0166 mg/ml ; 0.0000738 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

Safety of [ 174702-59-1 ]

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

Application In Synthesis of [ 174702-59-1 ]

* 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 [ 174702-59-1 ]
Downstream synthetic route of [ 174702-59-1 ]

[ 174702-59-1 ] Synthesis Path-Upstream 1~3

1
[ 869063-66-1 ]
[ 174702-59-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With thionyl chloride In dichloromethane	A mixture of this acid and 160 ml of SOCl₂ was stirred for 24 hours at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromophenyl)-2-methylpropionyl chloride dissolved in 270 ml of CH₂Cl₂ was added dropwise with vigorous stirring to a suspension of 136 g (1.02 mol) of AlCl₃ in 1350 ml of CH₂Cl₂ for 1 hour at 0° C. Then, this mixture was refluxed for 3 hours, cooled to ambient temperature, and poured on 500 cm³ of ice. The organic layer was separated. The aqueous layer was extracted with 3*300 ml of methyl-tert-butyl ether. The combined extract was dried over K₂CO₃ and evaporated to dryness. Fractional distillation gave 4-bromo-2-methyl-1-indanone, b.p. 131-134° C./2 mm Hg. Yield, 125.5 g (75percent) of a colorless solid. Anal. calc. for C₁₀H₉BrO: C, 53.36; H, 4.03. Found: C, 53.19; H, 3.98. ¹H NMR (300 MHz, CDCl₃): δ 7.76 (d, J=7.6 Hz, 1H, 7-H), 7.71 (d, J=7.6 Hz, 1H, 5-H), 7.28 (t, J=7.6 Hz, 1H, 6-H), 3.36 (dd, J=17.5 Hz, J=7.6 Hz, 1H, 3-H), 2.70-2.82 (m, 1H, 2-H), 2.67 (dd, J=17.5 Hz, J=3.8 Hz, 1H, 3'-H), 1.34 (d, J=7.3 Hz, 3H, 2-Me). ¹³C NMR (75 MHz, CDCl₃): δ 208.3, 152.9, 138.2, 137.2, 129.0, 122.6, 122.0, 41.8, 35.7, 16.0.

Reference： [1] Patent: US2007/135597, 2007, A1,
[2] Patent: WO2007/70040, 2007, A1, . Location in patent: Page/Page column 104-105
[3] Patent: WO2007/70041, 2007, A1, . Location in patent: Page/Page column 95-96

2
[ 19829-31-3 ]
[ 174702-59-1 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 9, p. 1775 - 1784

3
[ 174702-59-1 ]
[ 880652-93-7 ]

Reference： [1] Patent: EP2532687, 2012, A2,

[ 174702-59-1 ] Synthesis Path-Downstream 1~27

1
1-(3-Bromo-phenyl)-2-methyl-propenone [ No CAS ]
[ 174702-59-1 ]
6-bromo-2-methyl-2,3-dihydro-1H-inden-1-one [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1775 - 1784

2
[ 174702-59-1 ]
[ 880653-70-3 ]

Yield	Reaction Conditions	Operation in experiment
		38.3 g (1.02 mol) Of NaBH4 were added in small portions over 2 hours to a solution of 116 g (0.52 mol) of 4-bromo-2-methyl-l -indanone in 950 ml of THF-methanol (2:1, vol.) at -50C (Caution: temperature must be lower than O0C). The mixture was stirred overnight at ambient temperature. The resulting mixture was poured on 1000 cm3 of ice and acidified with 10% HCl to pH=4. The organic layer was separated, and the aqueous layer was extracted with 3 x 300 ml of methyl-tert-butyl ether. The organic fractions were combined and dried over K2CO3 and evaporated to dryness. To the residue 1500 ml of toluene were added. This toluene solution was treated with a catalytic amount of ^ToISO3H (ca. 2 g) for 2 hours at reflux. Then this mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 mum, d 60 mm, 1 40 mm). This <n="107"/>column was additionally eluted with 250 ml of toluene. The chromatographed product was evaporated to dryness. Fractional distillation gave a mixture of the title indene, b.p. 104-108C/5 mm Hg. Yield 100 g (93%) of colorless solid. Anal. calc. for C10H9Br: C, 57.44; H3 4.34. Found: C, 57.59; H, 4.40.1H NMR (CDCl3) of 7-bromo-2-methyl-lH-indene: delta 7.23 (dd, J= 7.9 Hz, J= 1.0 Hz, IH, 6-H), 7.18 (dd, J= 7.4 Hz, J= 1.0 Hz, IH, 4-H), 7.10 (m, IH, 5-H), 6.51 (m, IH, 3-H), 3.28 (m, 2H, 1,1'-H), 2.17 (s, 3H, 2-Me).13C NMR (CDCl3) of 7-bromo-2-methyl-lH-indene: delta 147.3, 146.8, 143.3, 128.2, 127.1, 126.6, 118.7, 118.3, 44.2, 16.7.
		To a solution of 1 16 g (0.52 mol) of 4-bromo-6-chloro-2-methyl-l- indanone in 950 ml of THF-methanol (2:1, vol.), 38.3 g (1.02 mol) Of NaBH4 were added in small portions for 2 h at -50C (Caution: temperature must be lower O0C). The mixture was stirred overnight at ambient temperature. The resulting mixture was poured on 1000 cm3 of ice and acidified with 10% HCl to pH=4. The organic layer was separated and the aqueous layer was extracted with 3 x 300 ml of methyl-ter/-butyl ether. This combined extract was dried over K2CO3 and evaporated to dryness. To the residue 1500 ml of toluene were added and the resulting toluene solution was treated with catalytic amount of ^ToISO3H (ca. 2 g) for 2 h at reflux. Then this mixture was cooled to room temperature and passed through a short Silica Gel 60 column (40-63 mum, d 60 mm, 1 40 mm). This <n="98"/>column was additionally eluted with 250 ml of toluene. The combined extract was evaporated to dryness. Fractional distillation gave a mixture of the title indenes, b.p. 104-108C/5 mm Hg. Yield 100 g (93%) of colorless solid.Anal. calc. for Ci0H9Br: C, 57.44; H, 4.34. Found: C, 57.59; H, 4.40.1H NMR (CDCl3): delta 7.23 (dd, J= 7.9 Hz, J= 1.0 Hz, IH, 6-H), 7.18 (dd, J= 7.4 Hz, J= 1.0 Hz, IH, 4-H), 7.10 (m, IH, 5-H), 6.51 (m, IH, 3-H), 3.28 (m, 2H, 1,1 '-H), 2.17 (s, 3H, 2-Me).13C NMR (CDCl3): delta 147.3, 146.8, 143.3, 128.2, 127.1, 126.6, 1 18.7, 1 18.3, 44.2, 16.7.

Reference： [1]Patent: WO2007/70040,2007,A1 .Location in patent: Page/Page column 105-106
[2]Patent: WO2007/70041,2007,A1 .Location in patent: Page/Page column 96-97

3
[ 19829-31-3 ]
[ 174702-59-1 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1775 - 1784

Yield	Reaction Conditions	Operation in experiment
		Illustrative examples of indanones of the formula Ia, which, however, do not restrict the scope of the invention, are: 2-methyl-4-chloro-1-indanone 2-methyl-4-bromo-1-indanone 2-methyl-4-iodo-1-indanone 2-methyl-4-trifluoroacetoxy-1-indanone 2-methyl-4-trifluoromethanesulfonoxy-1-indanone 2-methyl-4-methanesulfonoxy-1-indanone 2-methyl-4-ethanesulfonoxy-1-indanone 2-methyl-4-(p-toluenesulfonoxy)-1-indanone 2-methyl-4-benzenesulfonoxy-1-indanone ...

5
[ 880653-70-3 ]
[ 174702-59-1 ]
[ 880653-23-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; sodium tetrahydroborate; methyl iodide; In THF-methanol; water; dimethyl sulfoxide;	4-Bromo-1-methoxy-2-methylindane To a solution of 149.5 g (0.664 mol) of <strong>[174702-59-1]4-bromo-2-methyl-1-indanone</strong> in 900 ml of THF-methanol (2:1, vol.), 37.6 g (0.995 mol) of NaBH4 was added in small portions at vigorous stirring for 1.5 hours at 5 C. This mixture was stirred at room temperature for 12 hours and then added to 2 L of cold water. The hydrogenation product was extracted with 5200 ml of dichloromethane, and the combined extract was evaporated to dryness. To 149 g (2.65 mol) of KOH in 420 ml of DMSO, 188 g (82.5 ml, 1.33 mol) of MeI, and a solution of crude 4-bromo-2-methylindan-1-ol in 220 ml of DMSO were added. This mixture was stirred for 2 hours at ambient temperature; then, 92.0 g (40.4 ml, 0.664 mol) of MeI was added, and the mixture was additionally stirred for 2 hours. The resulting mixture was added to 2.5 L of cold water. The crude product was extracted with 5200 ml of dichloromethane. The combined extract was dried over Na2SO4 and, then, evaporated to dryness. Fractional distillation gave a mixture of two diastereomeric compounds, b.p. 108 C./3 mm Hg. Yield, 148.5 g (93%) of a colorless oil. Anal. calc. for C11H13BrO: C, 54.79; H, 5.43. Found: C, 54.86; H, 5.40. 1H NMR (300 MHz, CDCl3): delta 7.41 (d, J=7.9 Hz, 1H, 5-H of cis-product), 7.40 (d, J=7.9 Hz, 1H, 5-H of trans-product), 7.31 (d, J=7.2 Hz, 1H, 7-H of cis-product), 7.29 (d, J=7.2 Hz, 1H, 7-H of trans-product), 7.08 (m, 1H, 6-H of cis-product), 7.07 (m, 1H, 6-H of trans-product), 4.57 (d, J=5.8 Hz, 1H, CHOMe of trans-product), 4.45 (d, J=4.2 Hz, 1H, CHOMe of cis-product), 3.45 (m, 3H, OMe of cis-product), 3.40 (m, 3H, OMe of trans-product), 2.40-3.30 (m, 6H, CH2 and CHMe of cis-products), 1.18 (m, 3H, CHMe of cis-product), 1.11 (m, 3H, CHMe of trans-product). 13C{1H} NMR (75 MHz, CDCl3): delta 144.6, 144.1, 143.7, 143.4, 131.3, 131.2, 128.2, 127.8, 124.1, 123.9, 120.4 (two resonances), 91.9, 86.6, 56.9, 56.5, 39.7, 39.5, 39.0, 37.9, 19.2, 13.4.

Reference： [1]Patent: US2007/135597,2007,A1

6
[ 869063-66-1 ]
[ 174702-59-1 ]

Yield	Reaction Conditions	Operation in experiment
125.5 g (75%)	With thionyl chloride;AlCl3; In dichloromethane;	A mixture of this acid and 160 ml of SOCl2 was stirred for 24 hours at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromophenyl)-2-methylpropionyl chloride dissolved in 270 ml of CH2Cl2 was added dropwise with vigorous stirring to a suspension of 136 g (1.02 mol) of AlCl3 in 1350 ml of CH2Cl2 for 1 hour at 0 C. Then, this mixture was refluxed for 3 hours, cooled to ambient temperature, and poured on 500 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 3*300 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave 4-bromo-2-methyl-1-indanone, b.p. 131-134 C./2 mm Hg. Yield, 125.5 g (75%) of a colorless solid. Anal. calc. for C10H9BrO: C, 53.36; H, 4.03. Found: C, 53.19; H, 3.98. 1H NMR (300 MHz, CDCl3): delta 7.76 (d, J=7.6 Hz, 1H, 7-H), 7.71 (d, J=7.6 Hz, 1H, 5-H), 7.28 (t, J=7.6 Hz, 1H, 6-H), 3.36 (dd, J=17.5 Hz, J=7.6 Hz, 1H, 3-H), 2.70-2.82 (m, 1H, 2-H), 2.67 (dd, J=17.5 Hz, J=3.8 Hz, 1H, 3'-H), 1.34 (d, J=7.3 Hz, 3H, 2-Me). 13C NMR (75 MHz, CDCl3): delta 208.3, 152.9, 138.2, 137.2, 129.0, 122.6, 122.0, 41.8, 35.7, 16.0.
	With aluminum (III) chloride; In dichloromethane; at 0℃; for 4h;Heating / reflux;	In a three-necked round-bottom 2000 ml flask equipped with a reflux condenser, dropping funnel with pressure-equalizing, and magnetic stirring bar, 20.5 g (0.89 mol) of sodium metal were dissolved in 450 ml of dry ethanol. To the resulting solution 155 g (0.89 mol) of diethylmethylmalonate in 150 ml of dry ethanol was added drop wise within 15 minutes. This mixture was stirred for 15 minutes; then 186 g (0.89 mol) of °-bromobenzyl bromide was added, while vigorously stirring, at a rate that allowed the reaction mixture to maintain a gentle reflux. Additionally, this mixture was refluxed for 4 hours and cooled to room temperature. A solution of 151 g of potassium hydroxide in 400 ml of water was added. This mixture was refluxed for 3 hours to saponificate the ester formed. Ethanol and water were distilled off. To the residue, 500 ml of water and, then 12 M HCl (to pH 1) were added. The substituted methylmalonic acid that precipitated was separated, washed with 2 x 200 ml of cold water, and dried overnight on a watch glass. Crude 3-(2-bromophenyl)-2-methylpropanoic acid was obtained after decarboxylation of this substituted methylmalonic acid by heating it for 2 hours at 1600C. The product was used without further purification. A mixture of this acid and 160 ml of SOCl2 was stirred for 24 hours at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromophenyl)-2- methylpropionyl chloride dissolved in 270 ml of CH2Cl2 was added dropwise, while vigorously stirring, to a suspension of 136 g (1.02 mol) OfAlCl3 in 1350 ml OfCH2Cl2 over 1 hour at O0C. Then, this mixture was refluxed for 3 hours, cooled to ambient temperature, and poured on 500 cm3 of ice. The organic layer was <n="106"/>separated. The aqueous layer was extracted with 3 x 300 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title indanone, b.p. 131-134C/2 mm Hg. Yield 125.5 g (75%) of colorless solid.Anal. calc. for C10H9BrO: C, 53.36; H, 4.03. Found: C, 53.19; H, 3.98.1H NMR (CDCl3): delta 7.76 (d, J= 7.6 Hz, IH, 7-H), 7.71 (d, J= 7.6 Hz, IH, 5-H), 7.28 (t, J= 7.6 Hz3 IH, 6-H), 3.36 (dd, J= 17.5 Hz, J= 7.6 Hz, IH, 3-H), 2.70-2.82 (m, IH, 2-H), 2.67 (dd, J= 17.5 Hz, J= 3.8 Hz, IH, 3'-H), 1.34 (d, J= 7.3 Hz, 3H, 2-Me).13C NMR (CDCl3): delta 208.3, 152.9, 138.2, 137.2, 129.0, 122.6, 122.0, 41.8, 35.7, 16.0.
	With aluminum (III) chloride; In dichloromethane; at 0℃; for 4h;Heating / reflux;	In a three-necked round-bottom 2000 ml flask equipped with a reflux condenser, dropping funnel with pressure-equalizing, and magnetic stirring bar, 20.5 g (0.89 mol) of sodium metal were dissolved in 450 ml of dry ethanol. To the resulting solution 155 g (0.89 mol) of diethylmethylmalonate in 150 ml of dry ethanol were added dropwise within 15 min. This mixture was stirred for 15 min; then, 186 g (0.89 mol) of °-bromobenzyl bromide were added by vigorous stirring at a rate that allowed the reaction mixture to maintain a gentle reflux. Additionally, this mixture was refluxed for 4 h and cooled to room temperature. A solution of 151 g of KOH in 400 ml of water was added and the mixture was refluxed for 3 h to saponificate the ester formed. Ethanol and water were distilled off and 500 ml of water and, then, 12 M HCl (to pH 1) were added to the residue. The substituted methylmalonic acid that precipitated was separated, washed with 2 x 200 ml of cold water, and dried overnight on a watch glass. Crude 3-(2- bromophenyl)-2-methylpropanoic acid was obtained after decarboxylation of this substituted methylmalonic acid by heating it for 2 h at 160C. The product was used without further purification. Mixture of this acid and 160 ml of SOCl2 was stirred for 24 h at ambient temperature. Thionyl chloride was distilled off. The crude 3-(2-bromophenyl)-2-methylpropanoyl chloride dissolved in 270 ml of <n="97"/>CH2Cl2 was added dropwise by vigorous stirring to a suspension of 136 g (1.02 mol) of AlCl3 in 1350 ml of CH2Cl2 for 1 h at O0C. Then, this mixture was refluxed for 3 h, cooled to ambient temperature, and poured on 500 cm3 of ice. The organic layer was separated. The aqueous layer was extracted with 3 x 300 ml of methyl-te/7-butyl ether. The combined organic fractions were dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title indanone, b.p. 131-134C/2 mm Hg. Yield 125.5 g (75%) of colorless solid.Anal. calc. for C10H9BrO: C, 53.36; H, 4.03. Found: C, 53.19; H, 3.98.1H NMR (CDCl3): delta 7.76 (d, J= 7.6 Hz, IH, 7-H), 7.71 (d, J= 7.6 Hz, IH, 5-H), 7.28 (t, J= 7.6 Hz, IH, 6-H), 3.36 (dd, J= 17.5 Hz, J= 7.6 Hz, IH, 3-H), 2.70-2.82 (m, IH, 2-H), 2.67 (dd, J= 17.5 Hz, J= 3.8 Hz, IH, 3'-H), 1.34 (d, J= 7.3 Hz, 3H, 2-Me).13C NMR (CDCl3): 5 208.3, 152.9, 138.2, 137.2, 129.0, 122.6, 122.0, 41.8, 35.7, 16.0.

Reference： [1]Patent: US2007/135597,2007,A1
[2]Patent: WO2007/70040,2007,A1 .Location in patent: Page/Page column 104-105
[3]Patent: WO2007/70041,2007,A1 .Location in patent: Page/Page column 95-96

7
[ 174702-59-1 ]
[ 880652-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	With conc HCl; LiAlH4; toluene-4-sulfonic acid; In tetrahydrofuran; water; toluene;	Synthesis of 7-Bromo-2-methylindene. 5.57 g of <strong>[174702-59-1]4-Bromo-2-methylindanone</strong> (24.7 mmol) was dissolved in 45 mL of THF and added dropwise at -78 C to a suspension of 0.56 g of LiAlH4 (14.8 mmol) in 18 mL THF. Afterwards it was warmed to room temperature and stirred over night. Subsequently remaining LiAlH4 was hydrolyzed carefully at 0 C with 60 ml of water and 6 mL conc HCl. The mixture was extracted several times with Et2O. The combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After evaporation of the solvent the solid was dissolved in 60 mL toluene and 150 mg of p-toluene sulfonic acid was added. The mixture was stirred at reflux for 1 h. The resulting solution was washed with water, aqueous potassium hydroxide, water and saturated sodium chloride solution and dried over sodium sulfate. Evaporation of the solvent gave a slightly yellow solid. Yield 3.61 g (85 %). 1H NMR (CDCl3): delta 7.22 (m, 1H, H-Ar), 7.18 (d, J = 7.2 Hz, 1H, H-Ar), 7.10 (d, J = 7.6 Hz, 1H, H-Ar), 6.51 (m, 1H,=CH), 3.29 (s, 2H, CH2), 2.17 (s, 3H, CH3).

Reference： [1]Patent: EP2532687,2012,A2

8
[ 1516-96-7 ]
[ 174702-59-1 ]
C₂₅H₃₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		0.42 g (17.2 mmol) of a magnesium piece was charged into a 200 mL reactor thoroughly dried and purged with argon, and the mixture was vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. To this solution, Am. Chem. Soc. 2006, 128, 16486. A diluted solution of 4.67 g (15.6 mmol) of <strong>[1516-96-7]1-bromo-3,5-di-tert-butyl-4-methoxybenzene</strong> synthesized by the method described above in 25 mL of tetrahydrofuran was slowly added and heated under reflux in an oil bath for 1 hour did. After cooling the reaction solution to -78 C., 2.00 mL (18.0 mmol) of trimethoxyborane was slowly added and stirring was continued for 21 hours while gently returning to room temperature. A 1.0 M aqueous hydrochloric acid solution was added, the soluble matter was extracted with diethyl ether, and the obtained fraction was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the filtrate was distilled off, and the residue was added to a residue of Organometallics 2006, 25, 1217. 2.70 g (12.0 mmol) of 4-bromo-2-methyl-1-indanone synthesized by the described method, 6.69 g (31.5 mmol) of tripotassium phosphate, 0.03 g (0.13 mmol) of palladium acetate, 0.08 g (0.18 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl (S-Phos), 30 mL of tetrahydrofuran and 6 mL of distilled water were charged, At reflux for 2 hours. After the reaction solution was cooled to room temperature, a saturated aqueous solution of ammonium chloride was added and the soluble matter was extracted with ethyl acetate. The obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the filtrate was distilled off and the residue obtained was purified by silica gel column chromatography to give 4.09 g of the desired product (hereinafter referred to as the compound (1a)) represented by the following formula (1a) ( Yield 93%).
93%		Dry thoroughly, Into a 200 mL reactor purged with argon, 0.42 g (17.2 mmol) of a magnesium fragment were charged and stirred vigorously for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred.To this solution, Am. Chem. Soc. 2006, 128, 16486. A diluted solution of 4.67 g (15.6 mmol) of <strong>[1516-96-7]1-bromo-3,5-di-tert-butyl-4-methoxybenzene</strong> synthesized by the method described in 25 mL of tetrahydrofuran was added slowly,And heated under reflux in an oil bath for 1 hour. After the reaction solution was cooled to -78 C. 2.00 mL (18.0 mmol) of trimethoxyborane was slowly added and stirring was continued for 21 hours while gently returning to room temperature. A 1.0 M hydrochloric acid aqueous solution was added, the soluble matter was extracted with diethyl ether, The obtained fraction was washed with water and saturated brine, And dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the filtrate was distilled off to give a residue, Organometallics 2006, 25, 1217. 2.70 g (12.0 mmol) of 4-bromo-2-methyl-1-indanone synthesized by the described method, 6.69 g (31.5 mmol) of tripotassium phosphate,0.03 g (0.13 mmol) of palladium acetate,0.08 g (0.18 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(S-Phos) 30 mL of tetrahydrofuran, and 6 mL of distilled water were charged, And heated under reflux in an oil bath for 2 hours. After the reaction solution was cooled to room temperature, a saturated aqueous solution of ammonium chloride was added and the soluble matter was extracted with ethyl acetate. The obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate,The residue obtained by distilling off the filtrate was purified by silica gel column chromatography, 4.09 g (yield 93%) of the target compound (hereinafter referred to as compound (8a)) represented by the following formula (8a) was obtained

Reference： [1]Patent: JP2017/145209,2017,A .Location in patent: Paragraph 0246; 0247
[2]Patent: JP2017/145240,2017,A .Location in patent: Paragraph 0341; 0342

9
[ 174702-59-1 ]
C₂₆H₃₆Si [ No CAS ]