Water → HCID 89525057, compound

HRID 706342Notes

Reaction equation

HRID 706342 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][OH:7]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 43742622-(Hydroxymethyl)phenylboronic Acid

Product 1

HCID 89525057HCID 89525057, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of 2-bromothiazole (1.0 g, 6.1 mmol) in dioxane/water (20/5 mL) was added (2-(hydroxymethyl)phenyl)boronic acid (1.4 g, 9.1 mmol), sodium carbonate (1.29 g, 12.2 mmol), and Pd(PPh3)4 under nitrogen. The mixture was heated at reflux for 18 h. After cooling to rt, water (50 mL) was added and aqueous was extracted with DCM (3×50 mL). The combined organic layer was dried and evaporated. The residue was purified by column chromatography to yield (2-(thiazol-2-yl)phenyl)methanol (0.95 g, 5.1 mmol).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionaqueous was extracted with DCM (3×50 mL)
  4. customThe combined organic layer was dried
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9c16eb0770ed42178458b4ee116d9cd0
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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