Carbon tetrabromide → HCID 23045276, compound

HRID 2108123Notes

Reaction equation

HRID 2108123 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][O:33][CH2:34][CH2:35][CH2:36]O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[Br:39][CH2:36][CH2:35][CH2:34][O: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

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23045295HCID 23045295, compound

Product 1

HCID 23045276HCID 23045276, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (6.55 g) in dichloromethane (30 ml) was added dropwise to 3-[2-(4-phenylbutoxy)ethoxy]-1-propanol (5.0 g) and carbon tetrabromide (8.3 g) in dichloromethane (30 ml) at 0°. The mixture was stirred at room temperature for 1 h, evaporated onto silica, and purified by FCC eluting with cyclohexane - followed by System B (1:9) to give the title compound (5.4 g) as an oil. T.l.c. (System B 1:9) Rf 0.35

Workup

  1. customevaporated onto silica
  2. custompurified by FCC
  3. washeluting with cyclohexane -

Sources & evidence

ORD record
ord-e9034351e3b142d4a3cbd2d2e640a71b
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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