Carbon tetrabromide → 4-[(3-Bromopropyl)thio]-2,6-bis(1,1-dimethylethyl)phenol

HRID 1682542Notes

Reaction equation

HRID 1682542 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([C:24]1[CH:29]=[C:28]([S:30][CH2:31][CH2:32][CH2:33]O)[CH:27]=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:25]=1[OH:39])([CH3:23])[CH3:22].C(Br)(Br)(Br)[Br:41]>CCOCC>[Br:41][CH2:33][CH2:32][CH2:31][S:30][C:28]1[CH:29]=[C:24]([C:21]([CH3:23])([CH3:22])[CH3:20])[C:25]([OH:39])=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:27]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 214746842,6-Bis(1,1-dimethylethyl)-4-[(3-hydroxypropyl)thio]phenol

Product 1

HCID 190446984-[(3-Bromopropyl)thio]-2,6-bis(1,1-dimethylethyl)phenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triphenylphosphine (17.54 g, 66.89 mmol) was added to a stirred solution of 2 (9.9 g, 33.44 mmol) and carbon tetrabromide (22.18 g, 66.89 mmol) in dry ether. After stirring at room temperature for 18 hours, the reaction mixture was concentrated and the crude product was chromatographed (silica gel; hexane/ethyl acetate 98/2) to give 3 in quantitative yield. The structural assignment was supported by the 1H-NMR spectra in CDCl3.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe crude product was chromatographed (silica gel; hexane/ethyl acetate 98/2)
  3. customto give 3 in quantitative yield

Sources & evidence

ORD record
ord-b196dc17a74d4b98bb0678282b7b4b9e
Source dataset
uspto-grants-1997_06
Patent number
US05635514

Reaction notes

Loading…