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

HRID 1087030Notes

Reaction equation

HRID 1087030 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 0.054M 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 which 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 which

Sources & evidence

ORD record
ord-b2a0cd54b5fb48db98a24cff8a2a45cc
Source dataset
uspto-grants-1991_07
Patent number
US05034384

Reaction notes

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