3,5-DIBROMOBENZYL ALCOHOL
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3,5-DIBROMOBENZYL ALCOHOL
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CAS No:
145691-59-4
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Formula:
C7H6Br2O
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Chemical Name:
3,5-DIBROMOBENZYL ALCOHOL
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Synonyms:
RARECHEM AL BD 0770;3,5-DIBROMOBENZYL ALCOHOL;(3,5-DibroMophenyl)Methanol;1,3-Dibromo-5-hydroxymethylbenzene
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CAS No:
Safety Information
36/37/38
26-36/37/39
C
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
3,5-DIBROMOBENZYL ALCOHOL Use and Manufacturing
[4-[3, 5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid; 3, 5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0 °C. The reaction mixture was stirred for 0.5 h at 0 °C and then at 20 °C for another 0.5 h. The reaction mixture was con- centrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3 x 50 mL). Evaporation of the organic solution gave 3, 5-dibromo- benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84 percent). RF (Si02, hexanes/ethyl acetate 9:1) 0.25. Step 1 : To a stirred solution of 3, 5-dibromobenzoic acid (2 g, 7.168 mmol) in tetrahydrofuran (20 mL) was added borane dimethylsulfide (3.4 mL, 35.842 mmol, 5 eq.) at 0 °C, and the reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched with methanol at 0 °C and concentrated under vacuo to obtain (3, 5- dibromophenyl)methanol as an off white solid (1.8 g, 94percent). H NMR (400 MHz, DMSO-d6) δ ppm 4.47 (d, J = 6 Hz, 2H), 5.39 (t, J = 6 Hz, 1 H), 7.49 (s, 2H), 7.65 (s, 1 H).Step 1 : To a stirred solution of 3, 5-dibromobenzoic acid (2 g, 7.168 mmol) in tetrahydrofuran (20 mL) was added borane dimethylsulfide (3.4 mL, 35.842 mmol, 5 eq.) at 0 °C, and the reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched with methanol at 0 °C and concentrated under vacuo to obtain (3, 5- dibromophenyl)methanol as an off white solid (1.8 g, 94percent). H NMR (400 MHz, DMSO-d6) delta ppm 4.47 (d, J = 6 Hz, 2H), 5.39 (t, J = 6 Hz, 1 H), 7.49 (s, 2H), 7.65 (s, 1 H).General procedure: 3, 5-Di-t-butylbenzoic acid (5.00 g, 0.021 mol) was dissolved in anhydrous THF (250 mL) under argon atmosphere and the solution cooled to 0 °C. Lithium aluminum hydride (1.62 g, 0.043 mol) was added in small portions and the solution stirred at room temperature overnight. The reaction was quenched with water, Et2O (100 mL) was added and the mixture acidified with concentrated HCl solution until the solid residue was dissolved. The medium was extracted with Et2O and the organic phase dried over MgSO4, filtered and concentrated to yield 4.31g of 5a.Into a 100-mL round-bottom flask, was placed
Computed Properties
Molecular Weight:265.93
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:265.87649
Monoisotopic Mass:263.87854
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:97.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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