[ CAS No. 29578-83-4 ] {[proInfo.proName]}

Name: 29578-83-4|1-Bromo-3-methoxy-5-methylbenzene|97%
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Quality Control of [ 29578-83-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 29578-83-4 ]

CAS No. :	29578-83-4	MDL No. :	MFCD08061916
Formula :	C₈H₉BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AOEVRCZZWJWKPG-UHFFFAOYSA-N
M.W :	201.06	Pubchem ID :	10679554
Synonyms :

Calculated chemistry of [ 29578-83-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.6
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.54
Log Po/w (XLOGP3) :	2.95
Log Po/w (WLOGP) :	2.77
Log Po/w (MLOGP) :	2.88
Log Po/w (SILICOS-IT) :	2.96
Consensus Log Po/w :	2.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.0956 mg/ml ; 0.000475 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.314 mg/ml ; 0.00156 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0342 mg/ml ; 0.00017 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 29578-83-4 ]

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 [ 29578-83-4 ]

* 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 [ 29578-83-4 ]
Downstream synthetic route of [ 29578-83-4 ]

[ 29578-83-4 ] Synthesis Path-Upstream 1~18

1
[ 348169-39-1 ]
[ 29578-83-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: With hydrogenchloride; sodium nitrite In water; acetic acid at 0℃; for 0.5 h; Stage #2: With hypophosphorous acid In water; acetic acid at 0 - 20℃;	In a 250 ml round bottom flask, 4- bromo-2-methoxy-6-methyl-phenylamine (5.8 g, 26.84 mmol) was charged with acetic acid (49 mL) and concentrated HCl (5.6 mL). Sodium nitrite (2.19 g, 31.78 mmol) in 7 mL water was added to the mixture dropwise at 0 ⁰C. The reaction mixture was stirred at 0 ⁰C for 30 minutes. 50percent Hypophosphorous acid (56.5 mL) was added at 0 ⁰C. The reaction mixture was stirred at at 0 ⁰C, and warmed up to room, temperature overnight. Ethyl acetate was then added, followed by washing with saturated NaHCψ3 solution. The organic layer was concentrated and purified (silica gel, 100percent hexane) to give a pale liquid (5.12 g, 95percent). ¹H NMR (300 MHz, CDCb): δ 6.97(s, 1 H), 6.87 (s, 1 H), 6.64 (s, 1 H), 3.80 (s, 3 H), 2.36 (s, 3 H).
90%	Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water for 0.5 h; Cooling with ice Stage #2: With hypophosphorous acid In water at 0 - 20℃;	The reaction is performed in a water/ice bath. 500 mg (2.31 mmol, 1 eq) of 4-bromo-2-methoxy-6-methylaniline is dissolved in a mixture of 7 ml of acetic acid and 3 ml of water, followed by adding 0.8 ml of concentrated hydrochloric acid (37percent) and 207 mg (3.00 mmol, 1.5 eq) of sodium nitrite dissolved in 1 ml of water. The mixture is stirred for 30 min and subsequently added to 8 ml of ice-cooled 50percent by weight hypophosphoric acid. The reaction is stirred at 0° C. for 8 hours and allowed to stand at RT over night. For the processing, the mixture is extracted with ethyl acetate, dried over magnesium sulfate, filtered, and the solvent is removed in vacuum on a rotary evaporator. The raw product was not further purified (yield 90percent, 418 mg). C₈H₉BrO; MW 200/202; ¹H-NMR (CDCl₃): δ 6.45 (s, 1H), 6.39 (s, 1H), 6.18 (s, 1H), 3.30 (s, 3H), 1.83 (s, 3H); ¹³C-NMR (CDCl₃): δ 160.2, 141.0, 124.5, 122.4, 114.1, 113.9, 55.4, 21.2; IR: 2925, 1599, 1569, 1464 1/cm

Reference： [1] Patent: WO2009/5674, 2009, A2, . Location in patent: Page/Page column 423
[2] Patent: US2010/204234, 2010, A1, . Location in patent: Page/Page column 13-14
[3] Chemistry - A European Journal, 2005, vol. 11, # 3, p. 951 - 959
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[5] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[6] Patent: WO2008/124575, 2008, A1, . Location in patent: Page/Page column 138
[7] Patent: WO2008/124582, 2008, A1, . Location in patent: Page/Page column 118
[8] Patent: WO2007/147251, 2007, A1,

2
[ 74204-00-5 ]
[ 74-88-4 ]
[ 29578-83-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In acetone at 40℃; for 16 h;	To a mixture of 3-bromo-5-methyl-phenol (185 g; 0.940 mol) and K₂CO₃ (437 g, 3.17 mol) in acetone (2 L) is added MeI (424 g, 2.99 mol). The mixture is stirred at 40° C. for 16 h. The mixture is cooled to ambient temperature, filtered, and concentrated under reduced pressure. After filtration, the mixture is purified by flash silica gel chromatography to afford 1-Bromo-3-methoxy-5-methyl-benzene, D-4-1 (189 g, quant. yield) as a light yellow oil.
85.8%	With potassium carbonate In acetonitrile for 3 h; Reflux	C. Preparation of 3-methyl-5-methoxybromobenzene In a three-necked flask, 3-methyl 5-bromophenol (10.0 g, 53.5 mmol), potassium carbonate (22.2 g, 160.4 mol) andIodomethane (7.6 g, 53.5 mol) was dissolved in acetone (50 mL) and refluxed for 3 h. After the reaction is complete, add 30 mL of water, methylene chloride(50mL × 3) extraction, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure to give 3-methyl-5-methoxybromobenzene white.Crystals 9.2 g, yield 85.8percent
52%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24 h;	[0297] To the mixture of compound 29-1 (300 g, 1.6 mol) and K₂CO₃(665 g, 4.8 mol) in DMF (2000 mL) was added MeI (250 g, 1.8 mol) dropwised at room temperature. The mixture was stirred overnight. TLC showed the reaction is completed. The reaction was quenched by H₂O and extracted with EtOAc. The organic layer was dried, filtered, evaporated under reduced pressure to give the crude product which was purified by chromatography on silica gel to give compound 29-2 (165 g, 52percent yield).

Reference： [1] Patent: US2016/24059, 2016, A1, . Location in patent: Paragraph 0324-0325
[2] Patent: CN107501132, 2017, A, . Location in patent: Paragraph 0019-0121; 0034-0036; 0049-0051; 0064-0066
[3] Patent: US2014/73629, 2014, A1, . Location in patent: Paragraph 0297; 0313

3
[ 74137-36-3 ]
[ 74-88-4 ]
[ 29578-83-4 ]

Reference： [1] Patent: WO2008/43567, 2008, A1, . Location in patent: Page/Page column 32-33

4
[ 74204-00-5 ]
[ 29578-83-4 ]

Reference： [1] Patent: US4659706, 1987, A,

5
[ 50868-73-0 ]
[ 29578-83-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[2] Chemistry - A European Journal, 2005, vol. 11, # 3, p. 951 - 959
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[4] Patent: WO2007/147251, 2007, A1,
[5] Patent: WO2008/124582, 2008, A1,

6
[ 74204-00-5 ]
[ 77-78-1 ]
[ 29578-83-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1613 - 1620
[2] Chemische Berichte, 1921, vol. 54, p. 1311

7
[ 1357103-83-3 ]
[ 29578-83-4 ]

Reference： [1] Patent: WO2007/147251, 2007, A1, . Location in patent: Page/Page column 51-52

8
[ 58169-99-6 ]
[ 29578-83-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1613 - 1620

9
[ 849062-36-8 ]
[ 29578-83-4 ]

Reference： [1] Patent: CN107501132, 2017, A,

10
[ 1611-92-3 ]
[ 29578-83-4 ]

Reference： [1] Patent: CN107501132, 2017, A,

11
[ 82477-66-5 ]
[ 29578-83-4 ]

Reference： [1] Chem.Abstr., 1972, vol. 77, # 88083,

12
[ 66584-31-4 ]
[ 29578-83-4 ]

Reference： [1] Chem.Abstr., 1972, vol. 77, # 88083,

13
[ 29578-83-4 ]
[ 68-12-2 ]
[ 90674-26-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1 h; Stage #2: at -70℃; for 1 h;	To a mixture of D-4-1 (200 g, 0.995 mol) in dry THF (1.7 L), at −70° C., is added drop wise a solution of n-BuLi in hexanes (438 ml; 1.09 mol). After stirring for 1 h at −70° C., dry DMF (76.3 g, 1.04 mol) is added drop wise at −70° C. Following this, the mixture is stirred for 1 h at −70° C. The mixture is poured into NH₄Cl (1 L) and extracted with EtOAc. The combined extracted are washed with brine, dried over anhydrous Na₂SO₄and concentrated under reduced pressure to afford D-4-2 (147 g, 98percent yield) as a yellow oil.
147 g	With n-butyllithium In tetrahydrofuran at -70℃; for 2 h;	To a mixture of 25-02 (200 g, 0.995 mol) in dry THF (1.70 L) is added dropwise n-BuLi (438 ml; 1.09 mol) at -70° C. After stiffing for 1 h at -70° C., dry DMF (76.3 g, 1.04 mol) is added dropwise at -70° C. and stirred for 1 h at -70° C. The mixture is poured into NH₄Cl (1.00 L) and extracted with EtOAc (500 mL3), washed with brine (500 mL2), dried over Na₂SO₄ and concentrated to give 3-Methoxy-5-methyl-benzaldehyde, 25-03 (147 g) as a yellow oil.

Reference： [1] Journal of the American Chemical Society, 2018, vol. 140, # 15, p. 5065 - 5068
[2] Patent: US2016/24059, 2016, A1, . Location in patent: Paragraph 0324; 0326
[3] Patent: US2014/73629, 2014, A1, . Location in patent: Paragraph 0262

14
[ 29578-83-4 ]
[ 74204-00-5 ]

Reference： [1] Tetrahedron Letters, 1983, vol. 24, # 4, p. 377 - 380
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 5, p. 1278 - 1283

15
[ 29578-83-4 ]
[ 157893-14-6 ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine; potassium permanganate In water for 48 h; Reflux	). 1-Bromo-3-methoxy-5-methylbenzene (1.00 g, 5.0mmol) and pyridine/H₂O (2:5, 30 mL) were added to a round-bottomflask, followed by KMnO₄ (3.14 g, 20 mmol). The resulting mixturewas then heated while refluxing for 48 hr. After the removal of the precipitateby filtration, 2 M HCl was added to the reaction mixture to acidify it (pH 2).The aqueous phase was extracted with ethyl acetate. The organic phase waswashed with brine and dried over anhydrous Na₂SO₄. Thesolvent was removed under reduced pressure and the residue was purified usingsilica gel column chromatography. The white solid (385 mg, 34percent yield) wasidentified as 3-bromo-5-methoxybenzoic acid (3a) on the basis of ¹H-NMR spectra. ¹H-NMR(400 MHz, CDCl₃): d3.86(s, -OCH₃, 3H), 7.29 (t, J=2.0Hz, Ar H, 1H), 7.54 (t, J=2.0 Hz, ArH, 1H), 7.83 (t, J=2.0 Hz, Ar H, 1H).
24%	With pyridine; potassium permanganate In water at 105℃; for 24 h;	To a vigorously stirred mixture of 1-Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 ml_, 39.8 mmol) and Water (8 ml) was added in small portions KMnO ₄ (3.14g, 19.89 mmol) at 105°C. The mixture which turned to a black suspension was stirred 24 hours at 105°C, then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCI. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24percent yield) as a white solid. MS: 229.1 [M+H]⁺, Rt ^{(1 )} 1 .18 min.
24%	at 105℃; for 24 h;	To a vigorously stirred mixture of 1 -Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMn0₄ (3.14g, 19.89 mmol) at 105°C. The mixture which turned to a black suspension was stirred 24 hours at 105°C, then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCI. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24percent yield) as a white solid. MS: 229.1 [M+H]⁺, Rt ^{(1 )} = 1 .18 min.

24%

With pyridine; potassium permanganate In water at 105℃; for 24 h;

3-Bromo-5-methoxybenzoic acid
To a vigorously stirred mixture of 1-Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMnO₄ (3.14 g, 19.89 mmol) at 105° C.
The mixture which turned to a black suspension was stirred 24 hours at 105° C., then cooled down to RT and filtered over Hyflo.
The black residue was washed several times with EtOAc.
The filtrate was then diluted in EtAOc and washed with a 2M solution of HCl.
The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24percent yield) as a white solid. MS: 229.1 [M+H]⁺, Rt⁽¹⁾=1.18 min.

Reference： [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 4, p. 599 - 608
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4685 - 4698
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 23-24, p. 3708 - 3711
[4] Patent: WO2013/57711, 2013, A1, . Location in patent: Page/Page column 52-53
[5] Patent: WO2013/88404, 2013, A1, . Location in patent: Page/Page column 99
[6] Patent: US2015/342951, 2015, A1, . Location in patent: Paragraph 0869-0870

16
[ 29578-83-4 ]
[ 262450-65-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 4, p. 599 - 608

17
[ 29578-83-4 ]
[ 473923-98-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With copper(I) cyanide In DMF (N,N-dimethyl-formamide) at 60℃; for 20 h;	Three parallels of L-BROMO-3-METHOXY-5-METHYLBENZENE (Chan et al., supra) (2.00 g, 9.94 mmol) and CUCN (1.34 g, 15.0 mmol) in DMF (25 ml) was heated at 160 °C in sealed "Stemblock tubes"for 20 h. The parallels were combined, EtOAc was added and the mixture was filtered through a short plug of silica. The filtrate was purified by flash chromatography using 2-10percent EtOAc in hexanes. Yield 2.88 g (66percent); white solid. 'H NMR (400 MHz, CDC13) 8 2.33 (s, 3 H) 3.79 (s, 3 H) 6.92 (s, 2 H) 7.03 (s, 1 H). 13C NMR (100 MHZ, CDCL3) 8 21. 19,55. 40,112. 74,113. 88,118. 88,120. 01,125. 08,140. 75, 159.53. GC-MS: 100percent; 147 (M.

Reference： [1] Patent: WO2004/63156, 2004, A1, . Location in patent: Page 30-31

18
[ 29578-83-4 ]
[ 557-21-1 ]
[ 473923-98-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 90℃; for 7 h;	In a 100 mL round bottom flask, 1-bromo- 3-methoxy-5-methyl-berιzene (2.17 g, 10.79 mmol), Zn(CN)₂ (1.9 g, 16.19 mmol, 1.5 eq.) and Pd(PPro)4 ( 1.24 g, 1.08 mmol, 0.1 eq.) was charged with DMF (20 mL). The reaction mixture was heated at 90 ⁰C under Ar for 7 hours. Ethyl acetate was added, followed by washing with brine. The organic layer was concentrated and purified (silica gel, 0-50percent EtOAC/hexane) to give a white solid (1.31 g, 83percent). ¹H NMR (300 MHz, CDCb): δ 7.05(s, 1 H), 6.97 (s, 2 H), 3.81 (s, 3 H), 2.39 (s, 3 H).

Reference： [1] Patent: WO2009/5674, 2009, A2, . Location in patent: Page/Page column 423

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Yield	Reaction Conditions	Operation in experiment
86%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 12h;Inert atmosphere;	A mixture of NBS (5.31 g, 29.83 mmol, 1.20 equiv), AIBN (2.04 g, 12.42 mmol, 0.50 equiv), Cd4 (100 mL), and <strong>[29578-83-4]1-bromo-3-methoxy-5-methylbenzene</strong> (5.00 g, 24.87 mmol, 1.00 equiv) was stirred for 12 h at 80C under nitrogen. The reaction was then quenched by water, extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:100) to afford the title compound (6 g, 86%) as a light yellow solid.
63%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; at 45℃;	Add <strong>[29578-83-4]1-bromo-3-methoxy-5-methylbenzene</strong> 4a (22.8 g, 113 mmol) to the eggplant-shaped bottle, and dissolve in methylene chloride (100 mL) Add N-bromosuccinimide (242 g, 136 mmol) and azobisisobutyronitrile (31.5 g, 192 mmol) and heat to 45 C under reflux overnight. After the reaction is over,The reaction was returned to room temperature and extracted with ethyl acetate (40 mL x 3).The organic phase was washed with water (40 mL x 2) and brine (40 mL * 2),It was then dried over anhydrous sodium sulfate, filtered and concentrated.The obtained crude product was separated by a normal-phase silica gel column (petroleum ether: ethyl acetate = 20: 1) to obtain 1-bromo-3-(bromomethyl)-5-methoxybenzene 4b (20 g, yellow solid), yield : 63%.
42%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12h;Reflux;	[0298] The solution of compound 29-2 (100 g, 497.4 mmol), NBS (88.5 g, 497.4 mmol) and AIBN (10 g, 10%) in CCl4 (700 mL) was heated to reflux for 12 h. TLC showed the reaction is completed. After cooling down to room temperature, the reaction was quenched by H2O and extracted with EtOAc. The organic layer was dried, filtered and evaporated under reduced pressure to give the crude product which was purified by chromatography on silica gel to give compound 29-3 (48 g, 42% yield).

42%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12h;Reflux;	A mixture of D-6-1 (100 g, 497 mmol), NBS (88.5 g, 497 mmol), and AIBN (10 g, 50 mmol) in CCl4 (700 mL) is heated to reflux for 12 h. The mixture is cooled to ambient temperature, diluted with H2O, and extracted with EtOAc. The organic layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to afford D-6-2 (48 g, 42% yield).
38%	With N-Bromosuccinimide; In tetrachloromethane;Photochemical reaction;	1-BROMO-3-METHOXY-5-METHYLBENZENE (Chan et. al., J. Med. Chem. 2001, 44, 1866- 1882) (1.456 g, 7.286 mmol) and NBS (1.68 g, 9.46 mmol) in CC14 (20 ml) was irradiated (Rayonet, Photochemical Reactors) in a closed"Stemblock tube"overnight. A mixture of compounds was obtained as indicated by GC-MS of the reaction mixture. Flash chromatography using 2% EtOAc in hexanes gave 806 mg (38%) of a colorless oil ;-80% pure estimated from NMR. 'H NMR (400 MHz, CDC13) 8 3.79 (s, 3 H), 4.37 (s, 2 H), 6.84 (d, J=1.7 Hz, 1 H), 6.97-6. 98 (M, 1 H), 7.12-7. 12 (M, 1 H).
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	A mixture of <strong>[29578-83-4]5-bromo-3-methoxytoluene</strong> (20 g, 0.1 m), N-bromosuccinimide (17.8 g, 0.1 m) and dibenzoyl peroxide in carbon tetrachloride (200 ml) is heated to reflux and irradiated with a sunlamp. The mixture is cooled, filtered and concentrated in vacuo to give 5-bromo-3-methoxybenzyl bromide.
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	A mixture of <strong>[29578-83-4]5-bromo-3-methoxytoluene</strong> (20 g, 0.1 m), N-bromosuccinimide (17.8 g, 0.1 m) and dibenzoyl peroxide in carbon tetrachloride (200 ml) is heated to reflux and irradiated with a sunlamp. The mixture is cooled, filtered and concentrated in vacuo to give 5-bromo-3-methoxybenzyl bromide.
		Compound (1-2-1): Diethyl (3-Bromo-5-methoxybenzyl)phosphonate 5,5-Dimethyl-1,3-dibromohydantoin (13.1 g, 46 mmol) and azobisisobutyronitrile (1.50 g, 9.1 mmol) were simultaneously added at 80 C. to a solution of <strong>[29578-83-4]1-bromo-3-methoxy-5-methylbenzene</strong> (17.0 g, 91 mmol) synthesised by a method of the document (J. Med. Chem. 2001, 44, 1866) in monochlorobenzene (500 mL), and the reaction mixture was stirred at 80 C. for 30 minutes. The reaction solution was cooled to room temperature and then poured into a 10% aqueous sodium thiosulfate solution (100 mL), and the mixture was stirred for 30 minutes. The mixture was separated into aqueous and organic layers. The aqueous layer was subjected to extraction with toluene (100 mL). The combined organic layers were dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 1-bromo-3-(bromomethyl)-5-methoxybenzene. _

Yield	Reaction Conditions	Operation in experiment
87%	With sodium iodide; N,N`-dimethylethylenediamine;copper(l) iodide; In 1,4-dioxane; at 20 - 110℃; for 18h;Sealed tube; Inert atmosphere;	Example 1 Synthesis of (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene Cu(I)I (0.05 g, 0.25 mmol) and NaI (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 min. Anhydrous dioxane (5 mL), N,N'-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and <strong>[29578-83-4]1-bromo-3-methoxy-5-methylbenzene</strong> (1) (1.0 g, 5.0 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110 C. in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2Cl2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (2) (1.05 g, 87% yield) as a pale yellow oil.
87%	With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃; for 18h;Inert atmosphere; Sealed tube;	A. Cu(l)l (0.05 g, 0.25 mmol) and Nal (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 mi Anhydrous dioxane (5 mL), N,N-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and <strong>[29578-83-4]1-bromo-3-methoxy-5-methylbenzene</strong> (Compound No. 24, 1.0 g, 5 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110C in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2CI2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (Compound No. 25, 1.05 g, 87% yield) as a pale yellow oil.

Precautionary Statements-General
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P103	Read label before use
Prevention
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P320
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P321
P322
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 29578-83-4 ] {[proInfo.proName]}

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