N-bromobutanimide → 1-Bromo-2-(1-methylethyl)-4-(phenylmethoxy)benzene

HRID 2044186Notes

Reaction equation

HRID 2044186 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:18])=[C:11]([CH:15]([CH3:17])[CH3:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 129859311-(Benzyloxy)-3-(propan-2-yl)benzene

Product 1

HCID 129859321-Bromo-2-(1-methylethyl)-4-(phenylmethoxy)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 33 (452 mg, 2.00 mmol) in CCl4 (20 mL) were added N-bromosuccinimide (373 mg, 2.10 mmol) and silica gel (1 g) and the mixture was stirred in the dark at room temperature for 36 hours. Then, the mixture was filtered and the filtrates were washed with satured solution of sodium thiosulphate (10 mL). The organic phase were dried over Na2SO4, filtered and concentrated on vacuo to give 564 mg of bromoaryl 34. Yield 93%. 1H NMR (300 MHz, CDCl3) δ ppm: 7.32-7.51 (m, 6H), 6.92 (d, J=3.0 Hz, 1H), 6.68 (dd, J1=8.7 Hz, J2=3.0 Hz, 1H), 5.04 (s, 2H), 3.31 (sep, J=6.9 Hz, 1H), 1.22 (d, J=6.9 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ ppm: 158.4, 148.5, 136.7, 133.2, 128.6, 128.1, 127.5, 115.0, 114.0, 113.3, 70.2, 33.0, 22.7; HRMS (EI) m/z: calcd for C16H17BrO: 304.0463. found: 304.0465.

Workup

  1. filtrationThen, the mixture was filtered
  2. washthe filtrates were washed with satured solution of sodium thiosulphate (10 mL)
  3. dry with materialThe organic phase were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated on vacuo

Sources & evidence

ORD record
ord-719e384b8dda4ed6a545d12370e65d08
Source dataset
uspto-grants-2013_11
Patent number
US08586776B2

Reaction notes

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