Triphenylphosphine → HCID 15341856, compound

HRID 742101Notes

Reaction equation

HRID 742101 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH2:12]O)[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39]C(Cl)(Cl)C(Cl)(Cl)Br>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH2:12][Br:39])[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 11099403HCID 11099403, compound

Product 1

HCID 15341856HCID 15341856, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.00 g (12.3 mmol) 1-bromo-7-hydroxymethyl-4-isopropoxy-5-methoxy-naphthalene in 40 mL dry dichloromethane, 3.24 g (12.3 mmol) triphenylphosphane and 4.00 g (12.3 mmol) 1,2-dibromotetrachloroethane were added under Ar. After stirring for 30 min at room temperature, the solvent was removed and subsequently the residue was filtered over a short silica gel column (petroleum/ethyl acetate, 4:1) to give 5.00 g (95%) 1-bromo-7-bromomethyl-4-isopropoxy-5-methoxy-naphthalene as a colorless solid (m.p. 126° C.).

Workup

  1. customthe solvent was removed
  2. filtrationsubsequently the residue was filtered over a short silica gel column (petroleum/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-736ec69f52db43f1a42a64aff83210a5
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

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