Phosphate → 9H-Fluoren-9-one, 6-bromo-2-(hydroxymethyl)-

HRID 1493849Notes

Reaction equation

HRID 1493849 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([CH2:15][O:16]C(=O)C)[CH:8]=3.C[O-].[Na+].P([O-])([O-])([O-])=O>CO.C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([CH2:15][OH:16])[CH:8]=3

Participants

7

Reactant 3

HCID 1061PhosphateHCID 10758857HCID 10758857, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 105414109H-Fluoren-9-one, 6-bromo-2-(hydroxymethyl)-Yield 97.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-bromo-7-acetoxymethyl-9-fluorenone (1.18 g) was suspended in methanol (102 ml) and THF (23 ml). To this suspension was added 0.045M NaOMe (6.6 ml). The reaction mixture was stirred at room temperature for 1.25 hours. It was then neutralized with 0.2M pH 7 phosphate buffer. The tetrahydrofuran and methanol were removed under reduced pressure. Reaction mixture was then diluted with ethyl acetate, washed with water and brine, dried and evaporated gave the product (1.0 g).

Workup

  1. customThe tetrahydrofuran and methanol were removed under reduced pressure
  2. customReaction mixture
  3. washwashed with water and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-76fdc047da0a453ebd1b331112e78770
Source dataset
uspto-grants-1991_06
Patent number
US05025007

Reaction notes

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