Carbon tetrabromide → 4-Bromomethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

HRID 29330Notes

Reaction equation

HRID 29330 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][Br:38])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 687118924-Hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687165554-Bromomethyl-3-methylbenzofuran-2-carboxylic acid ethyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.200 g (0.855 mmol) 4-hydroxymethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester (Example 92, Step 2) in 5 mL of THF was added 0.336 g (1.28 mmol) of triphenylphosphine and 0.355 g (1.07 mmol) of carbon tetrabromide. The reaction was stirred at room temperature for 1 h and then concentrated in vacuo. The residue was diluted ith 20 mL of ether and filtered. The filtrate was concentrated in vacuo and chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.196 g of 4-bromomethyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted ith 20 mL of ether
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customchromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Sources & evidence

ORD record
ord-e5e6977b456a4c609d0fb01e8e1b1f9e
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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