Phosphorus oxide (P4O10) → 2-Acetoxy-5-bromo-6,6'-dimethyl-2', 3', 4'-trimethoxy-benzophenone

HRID 365957

Reaction equation

HRID 365957 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([CH3:15])[C:6]=1[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH3:28])[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([CH3:15])[C:6]=1[C:7]([C:19]1[C:20]([CH3:28])=[CH:21][C:22]([O:26][CH3:27])=[C:23]([O:24][CH3:25])[C:18]=1[O:17][CH3:16])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 110111492-Acetoxy-5-bromo-6-methylbenzoic acid

Product 1

HCID 109062512-Acetoxy-5-bromo-6,6'-dimethyl-2', 3', 4'-trimethoxy-benzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1C (6.83 g, 25 mmol), 3,4,5-trimethoxytoluene (4.56 g; 25 mmol), P2O5 (15.0 g) and dichloromethane (100 ml) is stirred at room temperature for 16 hours. Subsequently, the dichloromethane is distilled off and the residue is diluted with water and ethyl acetate. The organic phase is washed with water and concentrated. The residue is purified by preparative HPLC with acetonitrile:water 9:1 as eluent yielding the pure product as a yellow oil, 1.1 g, (10.1%).

Workup

  1. distillationSubsequently, the dichloromethane is distilled off
  2. additionthe residue is diluted with water and ethyl acetate
  3. washThe organic phase is washed with water
  4. concentrationconcentrated
  5. customThe residue is purified by preparative HPLC with acetonitrile:water 9:1 as eluent

Sources & evidence

ORD record
ord-4dc664032bb44c57911b3f9aacc56af6
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Linked notes

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