Thionyl Chloride → tert-Butyl [4-(chloromethyl)phenyl]carbamate

HRID 2067334Notes

Reaction equation

HRID 2067334 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>ClCCl.N1C=CC=CC=1>[Cl:19][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 10242688Boc-4-aminobenzylalcohol

Product 1

HCID 46835249tert-Butyl [4-(chloromethyl)phenyl]carbamateYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)-phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with water (25 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e98fc89cd874f068a4dfc2132c2176b
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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