Water → HCID 15617939, compound

HRID 703889Notes

Reaction equation

HRID 703889 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][CH2:15][CH2:16][P:17](=[O:24])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 15617938HCID 15617938, compound

Product 1

HCID 15617939HCID 15617939, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diethyl 4-(1-methoxy-2-naphthyl)-butylphosphonate (5.50 g 0.016 mole) in methylene chloride (80 mL) was stirred at -78°, and treated with boron tribromide (1.0M in methylene chloride; 24.0 mL, 0.024 mole) over 20 minutes. Stirring was continued for 2 hours at this temperature then at room temperature for 16 hours. Water (80 mL) was added, and the mixture was extracted with ether. The organic layer was extracted with 1.0N aqueous sodium hydroxide, the aqueous layer was acidified with concentrated hydrochloric acid, and the crude product was isolated from this by extraction with ether. The residue was recrystallized (hexane) to provide the title compound (2.10 g, 40%) as a white solid mp 90°-91°.

Workup

  1. waitat room temperature for 16 hours
  2. extractionthe mixture was extracted with ether
  3. extractionThe organic layer was extracted with 1.0N aqueous sodium hydroxide
  4. customthe crude product was isolated from this
  5. extractionby extraction with ether
  6. customThe residue was recrystallized (hexane)

Sources & evidence

ORD record
ord-8036496ff9ab45faa2532b72dbcbdf71
Source dataset
uspto-grants-1991_01
Patent number
US04985442

Reaction notes

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