Phosphorus tribromide → 5-Bromo-2-fluoro-4-methoxybenzyl bromide

HRID 518310Notes

Reaction equation

HRID 518310 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[C:7]([O:15][CH3:16])=[CH:8][C:9]([F:14])=[C:10]([CH2:12]O)[CH:11]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[C:10]([CH2:12][Br:2])[C:9]([F:14])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 53401483(5-Bromo-2-fluoro-4-methoxyphenyl)methanol

Product 1

HCID 978894395-Bromo-2-fluoro-4-methoxybenzyl bromideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

PBr3 (4.7 g, 17.4 mmol) was added drop-wise to a solution of (5-bromo-2-fluoro-4-methoxyphenyl)methanol (4.1 g, 17.4 mmol) in anhydrous CH2Cl2 (40 mL) at 0° C. The mixture was stirred at room temperature for 3 h and poured into ice water. The pH was adjusted to 8 with saturated aqueous NaHCO3. Extractive work up with CH2Cl2 gave the title compound (4.9 g, 94.8%) as a white solid which was carried on without purification. 1H NMR (DMSO-d6, 400 MHz) δ 7.56 (d, J=8.0 Hz, 1H), 6.65 (d, J=11.6 Hz, 1H), 4.46 (s, 2H), 3.89 (s, 3H).

Sources & evidence

ORD record
ord-c3579094cc2f42ffb7e4e04f2363c674
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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