Triethylamine → HCID 89649808, compound

HRID 2207623Notes

Reaction equation

HRID 2207623 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[Br:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[F:16])[NH2:12].C(N(CC)CC)C>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]([NH:12][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[CH:13]=[CH:14][C:15]=1[F:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 27792863-Bromo-4-fluoroaniline

Product 1

HCID 89649808HCID 89649808, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chlorobutanoyl chloride (4.12 mL, 36.84 mmol) in DCM (50 mL) was added over 15 mins to an ice-cooled solution of 3-bromo-4-fluoro-aniline (7 g, 36.84 mmol) and triethylamine (5.12 mL, 36.84 mmol) in DCM (100 mL) under N2. After addition was complete the cooling bath was removed and the solution stirred at ambient temp for 4 h. The reaction solution was washed with water (2×150 ml) dried (MgSO4) and concentrated to a white solid, which was dried at RT under vacuum overnight to give N-(3-bromo-4-fluoro-phenyl)-4-chloro-butanamide (D57) (9.04 g);

Workup

  1. additionAfter addition
  2. customwas removed
  3. washThe reaction solution was washed with water (2×150 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a white solid, which
  6. customwas dried at RT under vacuum overnight

Sources & evidence

ORD record
ord-24e985dc2f994bcc976d2f2dda338b41
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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