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

HRID 2178263

Reaction equation

HRID 2178263 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-de86bee2efba4b38a24505b38a0dd8ed
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Linked notes

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