Trimethyl orthoformate → HCID 66985986, compound

HRID 2069932Notes

Reaction equation

HRID 2069932 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)C=O.CO[CH:14]([O:17][CH3:18])[O:15][CH3:16].ClS(O)(=O)=O>CO>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:14]([O:15][CH3:16])[O:17][CH3:18])[C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 24638Chlorosulfonic acidHCID 110638083-Bromo-2-methoxybenzaldehyde

Product 1

HCID 66985986HCID 66985986, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Bromo-2-methoxybenzaldehyde (28 g, 130 mmol) was combined with trimethylorthoformate (27.5 g, 28.6 mL, 260 mmol) in methanol (150 mL) and then chlorosulfonic acid (0.5 mL) was added dropwise to the mixture. The mixture was stirred for 3 hours and then concentrated by rotoevaporation. The residue was partitioned between ethyl ether and 5% aqueous sodium bicarbonate and the organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated to give 1-bromo-3-dimethoxymethyl-2-methoxybenzene (27.5 g).

Workup

  1. concentrationconcentrated by rotoevaporation
  2. customThe residue was partitioned between ethyl ether and 5% aqueous sodium bicarbonate
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae096e5774284027bd8baaac623d7419
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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