N-bromobutanimide → HCID 86718024, compound

HRID 1500486Notes

Reaction equation

HRID 1500486 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH2:11][OH:12])[CH2:7][C:6]=2[CH:5]=[C:4]([CH3:13])[CH:3]=1.C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH2:11][OH:12])[CH2:7][C:6]=2[C:5]([Br:21])=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86718023HCID 86718023, compound

Product 1

HCID 86718024HCID 86718024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (7-amino-5-methyl-2,3-dihydrobenzofuran-2-yl)methanol (7d) (0.80 g, 4.5 mmol) in DMF (13 mL) at 0° C. was added NBS (0.08 g, 4.5 mmol), it was stirred at 0° C. for 15 min. The mixture was extracted with EtOAc (150 mL), washed with NaHSO3 (50 mL), water, brine, dried and concentrated to give the title compound (7e) as a yellow solid. MS-ESI (m/z): 258 (M+1)+.

Workup

  1. extractionThe mixture was extracted with EtOAc (150 mL)
  2. washwashed with NaHSO3 (50 mL), water, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23a310b275944ba0aab038bb817762c4
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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