Phosphorus oxide (P4O10) → 5-Bromo-6,6'-dimethyl-2-pivaloyloxy-2',3',4'-trimethoxybenzophenone

HRID 365961

Reaction equation

HRID 365961 reaction equation
[C:1]([O:7][C:8]1[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([CH3:18])[C:9]=1[C:10]([OH:12])=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH3:31])[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[Br:17][C:14]1[CH:15]=[CH:16][C:8]([O:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5])=[C:9]([C:13]=1[CH3:18])[C:10]([C:22]1[C:23]([CH3:31])=[CH:24][C:25]([O:29][CH3:30])=[C:26]([O:27][CH3:28])[C:21]=1[O:20][CH3:19])=[O:12]

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 809223,4,5-TrimethoxytolueneHCID 232932342-Pivaloyloxy-5-bromo-6-methylbenzoic acid

Product 1

HCID 226713735-Bromo-6,6'-dimethyl-2-pivaloyloxy-2',3',4'-trimethoxybenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 50A (6.3 g, 20 mmol), 3,4,5-trimethoxytoluene (3.83 g; 21 mmol), P2O5 (12.0 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 flash chromatography with petrol ethers/ethyl acetate (9:1 v/v) as eluent yielding the pure product as white crystals, 5.58 g, (58.2%).

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 flash chromatography with petrol ethers/ethyl acetate (9:1 v/v) as eluent

Sources & evidence

ORD record
ord-3051db69995040959e004c7e42720296
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Linked notes

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