Carbon tetrabromide → [4-[(6-Bromo-3-hexynyl)oxy]butyl]benzene

HRID 568877Notes

Reaction equation

HRID 568877 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]#[C:34][CH2:35][CH2:36]O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:39]>>[Br:39][CH2:36][CH2:35][C:34]#[C:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][CH2:27][CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 200713196-(4-Phenylbutoxy)-3-hexyn-1-ol

Product 1

HCID 20029810[4-[(6-Bromo-3-hexynyl)oxy]butyl]benzeneYield 88%

Procedure

Triphenylphosphine (4.5 g) in dry MC (20 ml) was added dropwise to the product of stage (i) (3.8 g) and carbon tetrabromide (5.8 g) in dry MC (50 ml) at 0°. The solution was stirred at 0° for 1 h and MC was evaporated. The residue was treated with ER (100 ml), filtered and the filtrate was evaporated. The residue was purified by FCC eluting with CX followed by CX-ER (4:1) to give the title compound as a colourless oil (4.2 g). T.l.c. (CX-ER 9:1) Rf 0.4.

Workup

  1. customMC was evaporated
  2. additionThe residue was treated with ER (100 ml)
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by FCC
  6. washeluting with CX

Sources & evidence

ORD record
ord-a82d16f2b17a4657b6cbb9875a427e28
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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