Bromine → tert-Butyl (3-bromo-4-oxocyclohexyl)carbamate

HRID 1402667Notes

Reaction equation

HRID 1402667 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:16]Br>O1CCCC1.C(OCC)C.[Cl-].[Al+3].[Cl-].[Cl-]>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([Br:16])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 24408BromineHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamate

Product 1

HCID 66611191tert-Butyl (3-bromo-4-oxocyclohexyl)carbamateYield 67%

Reagents, catalysts & solvents 3

HCID 6451240Aluminum(III) ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of (4-Oxo-cyclohexyl)-carbamic acid tert-butyl ester (10 grams, 46 mmol) and aluminum chloride (0.25 grams, 2 mmol) in tetrahydrofuran (30 mL) and diethyl ether (30 mL) was cooled to 0° C., then treated with bromine (2.4 mL, 46 mmol) over a period of 30 minutes. The reaction mass was stirred for 24 hours at 0-5° C. After completion of reaction, the obtained solids were filtered and lower filtrate was concentrated under vacuum. The obtained crude was triturated with diethyl ether and the resulted solids were filtered and dried under vacuum to obtain the title compound (9.0 grams).

Workup

  1. customAfter completion of reaction
  2. filtrationthe obtained solids were filtered
  3. concentrationlower filtrate was concentrated under vacuum
  4. customThe obtained crude
  5. customwas triturated with diethyl ether
  6. filtrationthe resulted solids were filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9239068aeb5a4bcab2eb70dec966b5d7
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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