N-bromobutanimide → 1345120-02-6

HRID 2272217Notes

Reaction equation

HRID 2272217 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[Br:11]C1C=CC(Cl)=CC=1O.C1C(=O)N(Br)C(=O)C1.BrC1OC2C=CC(Cl)=CC=2C1>C(#N)C>[Br:11][C:10]1[C:2]([Cl:1])=[CH:3][C:4]2[O:8][CH2:7][CH2:6][C:5]=2[CH:9]=1

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 132842722-Bromo-5-chlorophenolHCID 154670876-Chloro-2,3-dihydro-1-benzofuranHCID 67126933HCID 67126933, compound

Product 1

HCID 584872951345120-02-6

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar way as described above, 6-chloro-2,3-dihydrobenzofuran (142) was prepared starting from 2-bromo-5-chlorophenol. NBS (155 mg, 0.87 mmol) was added to a solution of 2-bromo-5-chloro-2,3-dihydrobenzo[b]furan (142) (135 mg, 0.87 mmol) in 5 ml ACN. The reaction mixture was stirred 5 h at r.t. The yellow solution was poured into ice-water, extracted with EA. Org. phase was washed with aq. sodium bicarbonate and brine subsequently. After dried over sodium sulfate the org. phase was concentrated to give 204 mg (purity>90%, quantitative yield) title compound as pale yellow solid.

Workup

  1. customwas prepared
  2. extractionextracted with EA
  3. washphase was washed with aq. sodium bicarbonate and brine subsequently
  4. dry with materialAfter dried over sodium sulfate the org
  5. concentrationphase was concentrated

Sources & evidence

ORD record
ord-03d46d173c4c439ca4c2d9d7c559bf93
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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