Boron tribromide → HCID 59557707, compound

HRID 1175317Notes

Reaction equation

HRID 1175317 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[O:18]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[OH:18]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 462061181-Bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene

Product 1

HCID 59557707HCID 59557707, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene (AS) (5.1 g, 15 mmol) in anhydrous CH2Cl2 (15 mL), the solution of BBr3 in CH2Cl2 (1M, 20 mL) was added dropwise at −5° C. After BBr3 was added, the reaction mixture was allowed to warm to room temperature and stirred for 2 h, after which TLC showed the reaction was complete. The reaction was quenched with saturated NaHCO3. The organic phase was separated and washed with water and brine. After drying with anhydrous Na2SO4, the organic portion was filtered and concentrated to give AT as an oil (4.49 g, yield 92%). 1H-NMR (CDCl3, 300 MHz) δ 7.22 (s, 1H), 7.13 (m, 4H), 7.07 (s, 1H), 5.42 (s, 1H), 3.99 (s, 2H), 2.54 (q, J=7.5 Hz, 2H), 1.23 (t, J=7.5 Hz, 3H).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialAfter drying with anhydrous Na2SO4
  5. filtrationthe organic portion was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd4dc16c453e42ddbc2c9385ef572046
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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