Carbon tetrabromide → 4-Tert-butyldimethylsilyloxy-3-propylbenzyl bromide

HRID 274938Notes

Reaction equation

HRID 274938 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=1[CH2:17][CH2:18][CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:40])=[CH:11][C:10]=1[CH2:17][CH2:18][CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54487098(4-{[tert-Butyl(dimethyl)silyl]oxy}-3-propylphenyl)methanol

Product 1

HCID 200892104-Tert-butyldimethylsilyloxy-3-propylbenzyl bromideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (3.57) of 4-tert-butyldimethylsilyloxy-3-propylbenzyl alcohol and 1.12 g (4.00 mmol) of triphenylphosphine in 10 mL methylene chloride was added 1.42 g (4.00 mmol) of carbon tetrabromide in portions as the reaction mixture was magnetically stirred at 0°-5° C. After the addition was complete, the ice-water bath was removed and the reaction was stirred for an additional 30 minutes and allowed to warm to room temperature. The methylene chloride was removed in vacuo, and the residue was applied to a silica gel flash chromatography column and eluted with 5% EtOAc-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 1.10 g (90%) of the title compound.

Workup

  1. additionAfter the addition
  2. customthe ice-water bath was removed
  3. stirringthe reaction was stirred for an additional 30 minutes
  4. customThe methylene chloride was removed in vacuo
  5. washeluted with 5% EtOAc-hexane
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-14612f8221a84ebb95ca08d05e49cd41
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

Loading…