Triethylamine → 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HRID 1840680Notes

Reaction equation

HRID 1840680 reaction equation
CN1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[C:5](=O)N(C)C1=O.COC1N=C(OC)C(B2OC(C)(C)C(C)(C)O2)=CN=1.CCN(CC)CC.[CH3:46][O:47][C:48]1C=C(Br)C=[CH:50][C:49]=1[OH:55].COC1C=C(C=C(B2OC(C)(C)C(C)(C)O2)C=1OC)C=O.B([O-])([O-])[O-]>>[CH3:46][O:47][C:48]1[CH:5]=[C:6]([B:8]2[O:9][C:10]([CH3:15])([CH3:16])[C:11]([CH3:13])([CH3:14])[O:12]2)[CH:7]=[CH:50][C:49]=1[OH:55]

Participants

7

Reactant 6

HCID 8471TriethylamineHCID 26574BorateHCID 2622344-Bromo-2-methoxyphenolHCID 162183882,4-Dimethoxypyrimidine-5-boronic acid pinacol esterHCID 164142251,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4(1H,3H)-pyrimidinedioneHCID 219239143,4-Dimethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Product 1

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Procedure

Solution 1 was transferred under N2 to a pressure-equalising dropping funnel and added to Solution 2 over 6 h. Stirred at RT overnight before heating at 40-50° C. for 8 h. After stirring overnight at RT a white ppt had formed. NEt3 (149 ml; 1.07 mol) was added followed by slow addition of 2-methoxy-4-bromophenol (91.6 g; 0.451 mol). Finally, the activated catalyst (Solution 3) was added and the resultant dark brown solution was stirred at 100° C. GC analysis after 20 hours showed the desired borate compound at 11.1 minutes (62%).

Workup

  1. temperaturebefore heating at 40-50° C. for 8 h
  2. stirringAfter stirring overnight at RT a white ppt
  3. customhad formed
  4. stirringthe resultant dark brown solution was stirred at 100° C
  5. waitGC analysis after 20 hours showed

Sources & evidence

ORD record
ord-e3b49df8d35f4ed48ce872fc4f512ff2
Source dataset
uspto-grants-2004_01
Patent number
US06680401B1

Reaction notes

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