N-bromobutanimide → 1345120-02-6

HRID 874647Notes

Reaction equation

HRID 874647 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-98881ed90491401b8848577c63b3fd4b
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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