Thionyl bromide → HCID 18761815, compound

HRID 432046Notes

Reaction equation

HRID 432046 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(Br)([Br:21])=O>C1(C)C=CC=CC=1>[Br:21][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 99211661-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

Product 1

HCID 18761815HCID 18761815, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5-hydroxymethyl-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (2 g, 8.2 mmol) in toluene (20 mL) was heated until the solid dissolved. Heating was then stopped. Thionyl bromide (2.2 g, 10.6 mmol) was added, and the mixture was stirred for 1 h. Silica (25 g) was added, and the mixture was filtered, and the residue was washed with a 1:1 v/v solution of ethyl acetate and heptane. The filtrate was evaporated to give the title compound as a red-orange oil (2.6 g, 90%). 1H NMR (d6-DMSO): δ 4.72 (s, 2H), 5.11 (d, 1H), 5.28 (d, 1H), 6.17 (s, 1H), 7.04 (d, 1H), 7.17 (t, 2H), 7.33 (d, 1H), 7.38 (dd, 2H), 7.45 (s, 1H).

Workup

  1. temperaturewas heated until the solid
  2. dissolutiondissolved
  3. temperatureHeating
  4. additionSilica (25 g) was added
  5. filtrationthe mixture was filtered
  6. washthe residue was washed with a 1:1 v/v solution of ethyl acetate and heptane
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a24a41cb4b4b43679ed8ced00790292f
Source dataset
uspto-grants-2003_12
Patent number
US06660873B2

Reaction notes

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