Structure of 4-Bromo-2-methyl-2-butanol
CAS No.: 35979-69-2
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 35979-69-2 |
Formula : | C5H11BrO |
M.W : | 167.04 |
SMILES Code : | CC(O)(C)CCBr |
MDL No. : | MFCD20483824 |
InChI Key : | RBFVGQWGOARJRU-UHFFFAOYSA-N |
Pubchem ID : | 10607172 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.1% | In tetrahydrofuran; at 0℃; | Intermediate 45 4-bromo-2-methylbutan-2-ol To a solution of methyl 3-bromopropanoate (0.2 g, 1.2 mmol,) in THF (5 mL) was added methyl magnesium bromide (2.4 mL, 2.4 mmol) at 0 C. The mixture was stirred at this temperature until the substrate was consumed based on tic [petroleum ether/ethyl acetate (3: 1); product Rf 0.3]. The reaction was quenched with ammonium chloride (2 mL) at 0 C. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated, to give a crude product which was purified by a column chromatography eluting with petroleum ether/ ethyl acetate (3: 1 ) to give 4-bromo-2- methylbutan-2-ol (0.15 g, 75.1 % yield) as a yellow oil. |
In diethyl ether; at 0℃; | a) 4-Bromo-2-methylbutan-2-olTo a cooled solution of ethyl 3-bromopropanoate (0.5 g, 2.8 mmol) in diethyl ether (50 ml) at 0 C was added methyl magnesium bromide (0.98 g, 8.3 mmol, 3 eq.) dropwise over 5 min and the mixture was allowed to stir until TLC showed complete absence of the starting material. The mixture was quenched and extracted as in Inter- mediate Example 5(c). The solvent was distilled off to give the crude product (0.4 g). | |
In diethyl ether; at 0℃; for 0.0833333h; | To a cooled solution of ethyl 3-bromopropanoate (0.5 g, 2.8 mmol) in diethyl ether (50 ml) at 0 C. was added methyl magnesium bromide (0.98 g, 8.3 mmol, 3 eq.) dropwise over 5 min and the mixture was allowed to stir until TLC showed complete absence of the starting material. The mixture was quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to give the crude product (0.4 g). |
In diethyl ether; at -20 - 20℃; for 2h; | Methyl magnesium bromide (11.04 mL, 33.14 mmol) was added drop wise over 10 min to a well-stirred mixture of ethyl 3-bromopropanoate (compound 24; 2.0 g, 11.04 mmol) in diethyl ether (25 mL) at -20 C. The reaction mixture was stirred at rt for over 2 h. On completion the reaction mixture was poured into aq. NH4Cl (25 mL) and extracted with EtOAc (2*25 mL). The combined organic layers were washed with H2O (100 mL) and brine (100 mL), separated and then dried over anhydrous Na2SO4. Evaporated under reduced pressure yielded 2.1 g of crude compound 25 which was used directly in the next step without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.7% | In diethyl ether; at -20℃; for 1h;Inert atmosphere; | In a 250 mL round bottom flask, methyl 3-bromopropanoate (5.0 mL, 45.8 mmol, 1.0 eq.) was taken up in dry ether (55.2 mL, 0.83 M) under nitrogen and cooled to -20 C. To this, 3.0 M methylmagnesium bromide (45.8 ml, 137 mmol, 3.0 eq) was added in dropwise fashion and the resulting mixture was stirred for an hour. The reaction was quenched with aqueous ammonium chloride. The resulting white suspension was extracted with ether multiple times. The combined organics were washed with brine, dried over MgSO4, and concentrated to yield 4-bromo-2-methylbutan-2-ol as an oil (5.49 g, 71.7%) |
65% | In diethyl ether; at 0 - 20℃; for 2h; | To a stirred solution of 4-bromo-butyric acid methyl ester (2 g, 12.27 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (16.4 mL, 49.08 mmol) at 0 C. and the mixture is stirred at room temperature for 2 hours. The reaction mixture is quenched with 1 N HCl and extracted with diethyl ether (2*20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified with silica gel column chromatography (combiflash) eluting in 20% EtOAc/hexanes to give the title compound (1.3 g, 65%). 1H NMR (400 MHz, CDCl3): δ 3.48 (t, J=8.0 Hz, 2H), 2.16 (t, J=7.4 Hz, 2H), 1.89 (s, 6H), 1.76 (s, 3H), 1.27 (s, 6H). |
60% | In diethyl ether; at 0 - 20℃; for 1h; | To a stirred solution of 4-bromo-butyric acid methyl ester (1 g, 5.9 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (19.9 mL, 23.9 mmol) at 0 C and the mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with aqueous ammonium chloride (40 mL) and extracted with diethyl ether (2x20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel column chromatography (combiflash) eluting with 20%EtOAc/hexanes to obtain title compound as pale pink liquid (0.6 g, 60%). ^NMR (400 MHz, DMSO) δ 4.38 (s, 1H), 3.52-3.48 (m, 2H), 1.97-1.91 (m, 2H), 1.08 (s, 6H). |
48.9% | In tetrahydrofuran; at 0 - 20℃; for 16h; | a) 4-Bromo-2-methylbutan-2-olTo a solution of methyl 3-bromopropanoate (5.0 g, 29.94 mmol, and 1.0 eq) in dry THF was added methyl magnesium bromide at 0C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50 % ethyl acetate in hexane). Yield 48.9 % (2.4 g). LC-MS (ESI): Calculated mass: 167.0; Observed massl67.1 [M+H]+ (it: 0.8-1.0 min). |
48.9% | In tetrahydrofuran; at 0 - 20℃; for 16h; | To a solution of methyl 3-bromopropanoate (5.0 g,29.94 mmol, and 1.0 eq) in dry THF was added methyl mag21 nesium bromide at 0 C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane). Yield 48.9% (2.4 g). LCMS (ESI): Calculatedmass: 167.0; Observedmass 167.1[M+ H] (it: 0.8-1.0mm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran; | (5) 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7-diene To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(acetylthiomethyl)androsta-5,7-diene (135 mg, 0.223 mmol) and <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (186 mg, 1.12 mmol) in tetrahydrofuran (1.5 ml), was added a 1M potassium hydroxide methanol solution (1.5 ml), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, followed by the addition of a saturated aqueous ammonium chloride solution and the extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was purified by preparative thin layer chromatography (4 sheets (each 0.5 mm thickness), dichloromethane:ethyl acetate=9:1, developed once) to give the titled compound (131 mg, 90%) as a colorless oil. IR(neat): 3388, 2954, 2929, 2897, 2856, 1462, 1377, 1254, 1099, 1082 cm-1. 1H NMR δ: 0.05 (s, 3H), 0.06 (s, 6H), 0.11 (s, 3H), 0.58 (s, 3H), 0.88 (s, 18H), 0.91 (s, 3H), 1.23 (s, 6H), 2.71 (dd, J=11.8, 5.1 Hz, 1H), 2.75-2.87 (m, 1H), 3.67-3.74 (m, 1H), 3.96-4.12 (m, 1H), 5.28-5.35 (m, 1H), 5.54-5.61 (m, 1H). MS m/z: 648 (M+), 459 (100%). UV λmax nm: 271, 282, 294. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In tetrahydrofuran; | (1) Synthesis of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene 17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (67.7 mg, 0.112 mmol), 1-bromo-3-hydroxy-3-methylbutane (93.5 mg, 0.560 mmol), 1M potassium hydroxide methanol solution (1 ml) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 31(1) (at room temperature for 30 min.), worked up and purified by preparative thin layer chromatography (2 sheets (each 0.5 mm thickness), hexane:ethyl acetate=3:1, developed once) to give the titled compound (67.4 mg, 93%) as a colorless oil. IR(neat): 3417, 2956, 2929, 2856, 1471, 1462, 1371, 1254, 1099, 1074 cm-1. 1H NMR δ: 0.05 (s, 3H), 0.07 (s, 3H), 0.07 (s, 3H), 0.11 (s, 3H), 0.85 (s, 3H), 0.88 (s, 9H), 0.89 (s, 9H), 0.95 (s, 3H), 1.24 (s, 6H), 2.59 (m, 2H), 2.85 (m, 1H), 3.23 (m, 2H), 3.71 (brs, 1H), 3.98-4.12 (m, 1H), 5.36-5.42 (m, 1H), 5.56-5.64 (m, 2H). MS m/z: 646 (M+), 457 (100%). UV λmax nm: 271, 281, 294. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; chloroform; | Preparation 2 3-Hydroxy-3-methylbutyl phenyl sulphone (Compound 21) To a solution of 4-bromo-2-methyl-2-trimethylsilyloxybutane (9) (12 g) in methanol (55 ml) at room temperature was added ethanolic hydrogen chloride (ca. 1M, 0.2 ml). After 10 minutes the solution was concentrated in vacuo (at room temperature) to constant weight. The residue was taken up in chloroform and reconcentrated to constant weight to give 4-bromo-2-methyl-2-butanol (H, y=1, R1 =R2 =Me) as a chromatographically homogenous oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.02 g (93%) | In N,N-dimethyl-formamide; pentane; | EXAMPLE 23 Preparation of 3-bromo-1,1-dimethylpropoxy)triethylsilane To a solution of 2.56 g (15.3 mmol) of <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong> and 4.86 g (71.4 mmol) of imidazole in 15 ml of dry N,N-dimethylformamide at 0 C. was added dropwise 6.48 g (43.0 mmol) of chlorotriethylsilane. The mixture was stirred at room temperature for 3 hours and 20 minutes, then quenched by adding ice chips. The mixture was diluted with water and extracted with pentane. The organic phase was washed with water, saturated brine, dried (Na2 SO4) and evaporated to dryness. The residue was chromatographed on silica gel (40-63μ) using pentane to give 4.02 g (93%) of 3-bromo-1,1-dimethylpropoxy)triethylsilane as an oil: IR (CHCl3) 838 cm-1; 1 H NMR (CDCl3) δ 0.58 (q, J=8 Hz, 6 H), 0.94 (t, J=8 Hz, 9 H), 2.03 (m, 2 H), 3.48 (m, 2 H); MS m/e 265 (M+ --CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.57 g (45%) | With hydrogenchloride; methylmagnesium bromide; In tetrahydrofuran; | EXAMPLE 22 Preparation of 4-bromo-2-methyl-2-butanol To a solution of 6.25 g (34.5 mmol) of ethyl 3-bromopropionate in 28 ml of dry tetrahydrofuran at -20 C. was added dropwise 28.8 ml (80.6 mmol) of 2.8M methylmagnesium bromide in ether. The mixture was stirred at room temperature for 2 hours and 50 minutes then quenched by addition of 15 ml of saturated aqueous ammonium chloride. After addition of 42 ml of 1N aqueous HCl, the organic phase was separated and the aqueous phase extracted with ether. The combined organic extracts were washed with saturated brine, dried (Na2 SO4) and evaporated to dryness. The residue was chromatographed on silica gel (40-63μ) using 30% ethyl acetate-hexane to give 2.57 g (45%) of 4-bromo-2-methyl-2-butanol as an oil: IR (CHCl3) 3605 cm-1; 1 H NMR (CDCl3) δ1.27 (s, 6 H), 1.33 (s, 1 H), 2.11 (m, 2 H), 3.51 (m, 2 H); MS m/e 151 (M+ --CH3). |