Dimethylformamide → Tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate

HRID 1641099

Reaction equation

HRID 1641099 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.CN(C=O)C>O>[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 59418705Tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 3-hydroxyphenylcarbamate (0.245 g, 1.17 mmol), K2CO3 (404 mg, 2.93 mmol), and 3-bromobenzyl bromide (322 mg, 1.29 mmol) was added anhydrous DMF (5 mL). The reaction mixture was heated to 60° C. for 18 hours. The reaction mixture was cooled to rt, poured into water and the resulting precipitate was collected by filtration and washed with water to provide the desired product tert-butyl 3-(3-bromobenzyloxy)phenylcarbamate (34A) with sufficient purity for subsequent use.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-5330b7f36fdc4b3ba4ad3f087e5197fc
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Linked notes

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