Carbon tetrabromide → tert-Butyl (6-bromohexyl)carbamate

HRID 522795Notes

Reaction equation

HRID 522795 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:36]>C1(C)C=CC=CC=1.O>[C:11]([O:10][C:9](=[O:15])[NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:36])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamate

Product 1

HCID 16211353tert-Butyl (6-bromohexyl)carbamateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of compound 2 (1 g, 4.61 mmol) in toluene (30 mL) were added Ph3P (1.81 g, 6.91 mmol) and CBr4 (2.29 g, 6.91 mmol) at RT under inert atmosphere and stirred for 3 h. The mixture was diluted with water (50 mL) and extracted with EtOAc (3×60 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude. The crude was purified (silica gel; 20% EtOAc/hexanes) to afford compound 3 (1 g, 78%) as colorless oil. 1H NMR (400 MHz, CDCl3): δ 4.51 (br s, 1H), 3.40 (t, J=6.8 Hz, 2H), 3.13-3.08 (m, 2H), 1.89-1.82 (m, 2H), 1.52-1.42 (m, 13H), 1.37-1.31 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×60 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude
  6. customThe crude was purified (silica gel; 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bf2d0c24b6ad4c21a5c94646a8eb0d3c
Source dataset
uspto-grants-2016_05
Patent number
US09334261B2

Reaction notes

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