Carbon tetrabromide → HCID 20062834, compound

HRID 2166155Notes

Reaction equation

HRID 2166155 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH2:26][CH2:27][O:28][CH2:29][C:30]#[C:31][CH2:32][CH2:33]O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:33][CH2:32][C:31]#[C:30][CH2:29][O: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 20062817HCID 20062817, compound

Product 1

HCID 20062834HCID 20062834, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (5.25 g) in dry DCM (15 ml) was added to a solution of the product of step (ii) (3.9 g) and carbon tetrabromide (6.63 g) in dry DCM (25 ml) at 0° over 10 min. The yellow solution was stirred at 0° for 30 min, evaporated onto silica (Merck 9385) and purified by FCC eluting with H→H-ER (3:1) to give the title compound as a colourless oil (2.7 g). T.l.c. (H-ER 2:1) Rf 0.69.

Workup

  1. customevaporated onto silica (Merck 9385)
  2. custompurified by FCC
  3. washeluting with H→H-ER (3:1)

Sources & evidence

ORD record
ord-006d27edad214f0dbc2169b910944382
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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