Carbon tetrabromide → 1,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamate

HRID 1789795

Reaction equation

HRID 1789795 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][Br:37])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridine

Product 1

HCID 220977361,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (8.00 g, 35.6 mmol) was dissolved in CH2Cl2 (150 mL) and treated with PPh3 (11.2 g, 42.8 mmol) under nitrogen. The reaction flask was cooled in an ice bath and CBr4 (14.2 g, 42.8 mmol) was added in small portions. The ice bath was removed after 30 min and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and acetonitrile (50 mL) was added. The reaction flask was placed in a refrigerator for 3 h and the precipitate filtered and washed with cold acetonitrile. The white solid was dried in vacuo giving (4-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (8.38 g, 82%).

Workup

  1. temperatureThe reaction flask was cooled in an ice bath
  2. customThe ice bath was removed after 30 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure and acetonitrile (50 mL)
  4. additionwas added
  5. waitThe reaction flask was placed in a refrigerator for 3 h
  6. filtrationthe precipitate filtered
  7. washwashed with cold acetonitrile
  8. customThe white solid was dried in vacuo

Sources & evidence

ORD record
ord-0d78069ce36d4a58bfce4e19432cccc4
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Linked notes

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