4-Bromobenzaldehyde → Benzyl 2-(Benzyloxy)-4-(4-Bromobenzylamino)Benzoate

HRID 81859Notes

Reaction equation

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=1.[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1>>[CH2:19]([O:18][C:4]1[CH:3]=[C:2]([NH:1][CH2:31][C:30]2[CH:33]=[CH:34][C:27]([Br:26])=[CH:28][CH:29]=2)[CH:17]=[CH:16][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 707414-Bromobenzaldehyde

HCID 66728439Benzyl 4-Amino-2-(Benzyloxy)Benzoate

Product 1

HCID 68076436Benzyl 2-(Benzyloxy)-4-(4-Bromobenzylamino)BenzoateYield 78%

Procedure

Primary aniline 1 was coupled to 4-bromobenzaldehyde on a 0.7 mmol scale via General Procedure A to furnish 2 (274 mg, 78%): δH (400 MHz, CDCl3) 4.12 (s, 2H, CH2, NHCH2Ph), 4.50 (br s, 1H, NH), 4.92 (s, 2H, CH2, CH2Ph), 5.18 (s, 2H, CH2, CH2Ph), 5.98 (d, J=1.8 Hz, 1H, CH (Ph)), 6.04 (dd, J=8.6 and 1.8 Hz, 1H, CH (Ph)), 7.02 (d, J=8.2 Hz, 2H, 2 CH (Ph)), 7.11-7.34 (m, 12H, 12 CH (Ph)), 7.70 (d, J=8.6 Hz, 1H, CH (Ph)); δC (100 MHz, CDCl3) 46.5, 65.4, 69.9, 97.0, 104.5, 108.2, 120.7, 126.4, 127.2, 127.4, 127.6, 128.0, 128.1, 128.4, 131.4, 133.9, 136.3, 137.0, 152.3, 160.4, 165.3; LRMS (ES+) calcd for [C28H24BrNO3+H] 502.10. found 502.06.

Sources & evidence

ORD record: ord-5818dc81eee64491944c73339a0af8da
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846707B2

Reaction notes

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