Carbon tetrabromide → HCID 11531974, compound

HRID 2356104Notes

Reaction equation

HRID 2356104 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)=O.[C:21](Br)(Br)([Br:23])[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][C:21]([Br:23])=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[C:5]([O:19][CH3:20])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11558086Methyl 4'-formyl-2'-methoxy[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 11531974HCID 11531974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 122I (1.35 g, 5.0 mmol) in dichloromethane (30 mL) at room temperature was treated with carbon tetrabromide (1.82 g, 5.5 mmol) and triphenylphosphine (2.88 g, 11 mmol), stirred for 1 hour, treated with hexanes (50 mL), and filtered through silica gel (50 g). The solution was rinsed with 1:1 water/dichloromethane, separated, and the organic phase was concentrated. The concentrate was purified by flash column chromatography on silica gel with 2-10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered through silica gel (50 g)
  2. washThe solution was rinsed with 1:1 water/dichloromethane
  3. customseparated
  4. concentrationthe organic phase was concentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 2-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e87267936b984c7fa59c899f95a2bffc
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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