Bromine → HCID 68961434, compound

HRID 2116094Notes

Reaction equation

HRID 2116094 reaction equation
[Br:1][CH2:2][C@H:3]1[CH2:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[O:4]1.[Br:13]Br>C(O)(=O)C.CO>[Br:13][C:11]1[C:5]2[O:4][C@@H:3]([CH2:2][Br:1])[CH2:7][C:6]=2[CH:8]=[C:9]([F:12])[CH:10]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 16655467HCID 16655467, compound

Product 1

HCID 68961434HCID 68961434, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of (R)-2-bromomethyl-5-fluoro-2,3-dihydro-benzofuran (3.20 g, 14 mmol) in acetic acid was added bromine (2.2 ml, 42 mmol) and the reaction mixture was allowed to stir at room temperature for 12 h. The solvent was removed in vacuo and the residue dissolved in dichloromethane and washed with saturated aqueous sodium sulfite. The solvent was removed in vacuo and purification by flash column chromatography (silica, ethyl acetate:hexanes 1:19) afforded 3.16 g (74%) of as a light yellow oil. HRMS EI m/e 307.8846 (M)+, Calc'd. 307.8848. [α]D25=+24.8 (c 1% in methanol).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium sulfite
  4. customThe solvent was removed in vacuo and purification by flash column chromatography (silica, ethyl acetate:hexanes 1:19)
  5. customafforded 3.16 g (74%) of as a light yellow oil

Sources & evidence

ORD record
ord-b13143e84ac04df8a2beab206ca87b18
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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