3-Fluoro-5-bromophenol
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3-Fluoro-5-bromophenol
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CAS No:
433939-27-6
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Formula:
C6H4BrFO
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Chemical Name:
3-Fluoro-5-bromophenol
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Synonyms:
3-FLUORO-5-BROMOPHENOL;3-BROMO-5-FLUOROPHENOL;5-BROMO-3-FLUOROPHENOL;3-FLUORO-5-BROMO PHENOL,=98%
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CAS No:
Safety Information
IRRITANT
NONH for all modes of transport
3
22-36/37/38
26
Xi,Xn
Irritant
P261-P305 + P351 + P338
H302-H315-H319-H335
|Warning|H302 (97.56%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Fluoro-5-bromophenol Use and Manufacturing
To a solution of l-bromo-3, 5-difluorobenzene (30.6 mL, 0.266 mole) and 2-(methylsulfonyl)ethanol (66 g, 0.531 mole) in DMSO (240 mL) was added potassium tert-butoxide (76.6 g, 0.682 mole) at 0To a solution of 1-bromo-3-fluoro-5-benzyloxybenzene (110.0 g, 0.39 mol; see step (i) above) and N, N-dimethylaniline (474.0 g, 3.92 mol) in anhydrous CHTo a solution of 1-bromo-3-fluoro-5-benzyloxybenzene (110.0 g, 0.39 mol; see step (i) above) and N, N-dimethylaniline (474.0 g, 3.92 mol) in anhydrous [CH2CI2] (1.0 L) at [0°C] was added aluminium chloride (156.0 g, 1.17 mol). After 10 min, the ice bath was removed and the stirring was continued for 2 h. The reaction was quenched by the cautious addition of 3N HC1 (600 mL). The layers were separated, and the aqueous layer was extracted with [CH2CI2] (2 x 150 mL). The combined organic extracts were washed with 2N HCI (250 mL) and [H2O] (3 x 250 mL). To the organic layer was added 15percent KOH (500 mL), and the layers were separated. The organic layer was further extracted with 2 N KOH (2 x 70 mL). The combined aqueous layers were washed with [CH2CI2] (3 x 100 [ML)] and then acidified with 4N HCI. The aqueous layer was extracted with [ET, ] O [X 1 ' 5] mL) then, the combined Et20 extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the sub-title compound (69.0 g, 92percent) as a brown oil that was used without further purification. Mp: [33-35°C] Rf = 0.25 (CHC13) 'H NMR (300 MHz, DMSO-d6) 8 10.38 (s, 1H), 6.90 (dd, [JH-F] = [11 HZ, J] = 2 Hz, 1H), 6.81 (s, [1H), ] 6.59 (dt, JH-F = 11 Hz, [J] = 2 Hz, [1H).] APCI-MS: (M-1) = 189 m/z3-bromo-5-fluoro-phenol Step 2 To a stirred suspension of l-bromo-3-fluoro-5-methoxybenzene (5.0 g, 25 mmol) in DCM (50 mL) was added BBr