Methanesulfonic Acid → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene

HRID 1713589Notes

Reaction equation

HRID 1713589 reaction equation
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([Cl:18])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:7]=1.C([SiH](CC)CC)C.CS(O)(=O)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 12052TriethylsilaneHCID 46206796(5-Bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone

Product 1

HCID 462061181-Bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone (21) (5.6 g, 69%) was dissolved in trifluoroacetic acid (40 mL). To this mixture was added triethylsilane (6.3 mL, 40 mmol) and methanesulfonic acid (0.40 mL, 6.0 mmol). The resulting solution was stirred at room temperature for 2.5 hours, after which it was partitioned between water and ethyl acetate. The organic layer was washed with water (1×25 mL), followed by saturated NaHCO3 (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered, and evaporated. Silica gel chromatography with 0-10% ethyl acetate in hexane gave the title compound (4.7 g, 88%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.09-7.04 (m, 4H), 6.88 (s, 1H), 3.95 (s, 2H), 3.84 (s, 3H), 2.61 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

Workup

  1. customafter which it was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with water (1×25 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ce7a0c9885464cb58f0362a8b14821b5
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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